CHAPTER - 3. SYNTHESIS OF INDENO[1,2-d]PYRIMIDINE-2-THIONES AND EXPERIMENTAL. plates and spots were located by iodine vapours. Infra red spectra were
|
|
- Alexandrina Russell
- 5 years ago
- Views:
Transcription
1 CAPTER - 3 YTEI OF IDEO[1,2-d]PYRIMIDIE-2-TIOE AD TEIR ALKYL/ARALKYL DERIVATIVE EXPERIMETAL Melting points were determined in open end capillaries and are uncorrected. Compounds were checked for their purity by TLC on silica gel G plates and spots were located by iodine vapours. Infra red spectra were recorded on Perkin-Elmer RX IFT-IR system using KBr pellets. Proton magnetic resonance spectra were recorded on Bruker Advance II 400 MR spectrometer with tetra methyl silane as internal standard. Mass spectra were recorded by the ational Institute of Pharmaceutical Research (IPER), Mohali. The microwave irradiated reactions were performed in domestic household microwave oven amsung M177. For all the reactions, chemicals of igma Aldrich standard were used. All solvents were distilled before use. YTEI OF 4-UBTITUTED PEYL-1,3,4,5-TETRAYDRO- 2-IDEO[1,2-d]PYRIMIDIE-2-TIOE General Procedure 117
2 A mixture of 1-indanone (0.01 mole, 1.32g), thiourea (0.01mole, 0.76g) and substituted aromatic aldehydes (0.01 mole) were irradiated in unmodified domestic microwave oven (at 30% microwave power) using absolute alcohol (5 ml) as an energy transfer medium and conc. Cl (3-4 drops) as a catalyst. The same reaction was also carried out through thermal heating. The reaction was monitored by thin layer chromatography (TLC) using silica gel-g plates. Ethyl acetate and n-hexane mixture was used as eluting solvent taken in ratio of 1:1. After drying of plates in air, spots were marked and exposed to iodine chamber. The reaction mixture on standing for a few hours afforded solid product which was filtered under reduced pressure and recrystallized out of alcohol. A typical procedure is given below: (VIIa) 4-(4-Methoxyphenyl)-1,3,4,5-tetrahydro-2-indeno[1,2-d] pyrimidine-2-thione A mixture of 1-indanone (0.01 mole, 1.32 g), 4-methoxy benzaldehyde ( 0.01 mole, 1.36 ml), thiourea (0.01 mole, 0.76 g) and concentrated Cl (3-4 drops) was dissolved in absolute alcohol (5 ml) taken in borosil beaker (100 ml) and was irradiated in unmodified domestic microwave oven at 30% microwave power for 8.00 min. The same reaction mixture was refluxed. But, 118
3 it took 5.30 hrs. to complete the reaction. The reaction was monitored by thin layer chromatography (TLC) using silica gel-g plates. Ethyl acetate and n- hexane mixture was used as eluting solvent (1:1). After drying the plates, spots were exposed to iodine chamber. The reaction mixture on standing for a few hours afforded solid product which was filtered under reduced pressure and recrystallized out of alcohol for 2-3 times to give pure product. M.P. = C. Yield = 52 %. PMR (CDCl 3 DMO) : 8.26 (s, 1, ), 7.94 (s, 1, ), (m, 8, Ar- ), 5.66 (s, 1, 4- C), 4.00 (s, 2, C 5 C 2 ), 3.88 (s, 3, OC 3 ) Mass fragments (m/z): 308 M, 307, 249, 188, 178, 129, 120 IR (KBr) cm -1 : (- str), & (C- str), (C=C str). 119
4 Other compounds (VII b VII j) were also synthesized similarly and are listed in Table 6 along with their characterization data. O CO 2 R 2 C 30 % w Conc. Cl abs. alcohol R VIIa-VIIj TABLE 6 CARACTERIZATIO DATA OF PRODUCT (VIIa VIIj):. o M.P. Microwave Reflux Microwave Reflux Compd R Reaction time % Yield a Time (min) Time (hrs) ( 0 C) VIIa 4-OC VIIb 3-O VIIc 2,3-(O-C O) VIId 4-O,3-OC
5 VIIe 4-O VIIf 2-C VIIg 2,4-(Cl) VIIh 2-O VIIi VIIj 4-(C 3 ) a Yield of crude product pectral data of compounds (VIIb-VIIi) are listed below: (VIIb) PMR (CDCl 3 DMO) : (s, 1, ), 8.90 (s, 1, ), (m, 8, Ar-), 5.68 (s, 1, 4-C), 4.13 (s, 2, C 5 C 2 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), & (O 2 ), (C --- C), (C-), (C=). 121
6 Mass fragments (m/z): 323 M, 264, 201, 188, 135, 114, 92. (VIIc) PMR (CDCl 3 DMO) : 8.50 (s, 1, ), (m, 8, Ar- & -), 6.06 (s, 2, O-C 2 - O), 5.42 (s, 1, 4-C), 4.01 (s, 2, C 5 C 2 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), (C --- C), (C-), (C=). (VIId) PMR (CDCl 3 DMO) : 9.96 (s, 1, O-), 8.78 (s, 1, ), (m, 8, Ar- & -), 5.45 (s, 1, 4-C), 4.09 (s, 2, C 5 C 2 ), 3.79 (s, 3, OC 3 ). IR (KBr, cm -1 ): (O-), (- str.), (C- str.), (C=C str.), (C --- C), (C-), (C=). (VIIe) PMR (CDCl 3 DMO) : 122
7 10.56 (s, 1, ), 8.78 (s, 1, ), (m, 8, Ar-), 5.55 (s, 1, 4-C), 4.11 (s, 2, C 5 C 2 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), & (O 2 ), (C --- C), (C-), (C=). (VIIf) PMR (CDCl 3 DMO) : 9.62 (s, 1, ), 8.65 (s, 1, ), (m, 8, Ar-), 5.48 (s, 1, 4-C), 4.02 (s, 2, C 5 C 2 ), 1.23 (s, 3, C 3 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), (C --- C), (C-), (C=). (VIIg) PMR (CDCl 3 DMO) : 8.42 (s, 1, ), (m, 7, Ar-), 6.86 (s, 1, -), 6.08 (s, 1,4-C), (d, 1, C 5 C 2 ), (d, 1, C 5 C 2 ). IR (KBr, cm -1 ): 123
8 (- str.), (C- str.), (C=C str.), 1528 (C --- C), (C-), (C=). (VIIh) PMR (CDCl 3 DMO) : (s, 1, ), 8.76 (s, 1, ), (m, 8, Ar-), 5.62 (s, 1, 4-C), 4.10 (s, 2, C 5 C 2 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), & (O 2 ), (C --- C), (C-), (C=). (VIIi) PMR (CDCl 3 DMO) : (s, 1, ), 8.57 (s, 1, -), (m, 9, Ar-), 5.51 (s, 1, 4-C), 4.21 (s, 2, C 5 C 2 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), (C --- C), (C-), (C=). Mass fragments (m/z): 278 M, 277, 218, 201,188, 173, 149, 129, 114, 105, 90, 77,
9 YTEI OF 2-(METYLTIO)-4-ARYL-4,5-DIYDRO-1- IDEO[1,2-d]PYRIMIDIE General Procedure Indeno[1,2-d]pyrimidine-2-thiones (0.004 mole) were dissolved in 25 ml ethanol. To it, added ao solution, which was prepared by dissolving ao (0.004 mole, g) in water (2 ml). The reaction mixture was cooled. To this cold mixture, dimethyl sulphate (0.5 ml, mole) was added dropwise while stirring the mixture continuously. The reaction mixture was refluxed for 3 hours. The reaction was monitored by thin layer chromatography (TLC) using silica gel-g plates. Ethyl acetate and n-hexane mixture (1:1) was used as eluting solvents and used as eluting solvents and spots were exposed to iodine chamber. The mixture was cooled and poured over crushed ice. olid separated was filtered under reduced pressure, washed with ethanol and dried. It was recrystallized from ethanol to provide a pure sample of the product. 125
10 A typical procedure is given below: VIIIa 2-(methylthio)-4-(4-methoxyphenyl)-4,5-dihydro-1indeno [1,2-d]pyrimidines 4-(4-Methoxyphenyl)-1,3,4,5-tetrahydro-2-indeno[1,2- d]pyrimidine-2-thione Ia (0.004 mole, 1.232g) was dissolved in 25 ml ethanol. To it, added ao solution, which was prepared by dissolving ao (0.004 mole, g) in water (2 ml). The mixture was cooled. To this mixture, dimethyl sulphate (0.5 ml, mole) was added dropwise while stirring the mixture continuously. Then, the reaction mixture was refluxed for 3 hours. The reaction was monitored by thin layer chromatography (TLC) using silica gel-g plates. Ethyl acetate and n- hexane mixture was used as eluting solvents (1:1) and after drying, the plates were exposed to iodine chamber. The reaction mixture was cooled and poured over crushed ice. olid separated was filtered under reduced pressure, washed with ethanol and dried. It was recrystallized from ethanol to provide a pure sample of the product. M.P. = C Yield = 39% PMR (CDCl 3 DMO) : 126
11 (m, 9, Ar- & ), 5.35 (s, 1, 4-C), 4.10 (s, 2, C 5 C 2 ), 3.89 (s, 3, OC 3 ), 2.72 (s, 3, -C 3 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), (C --- C), (C-). Mass fragments (m/z): 322 M, 321, 320, 289, 274, 178, 167, 155, 129, 77 (VIIIb) PMR (CDCl 3 DMO) : 9.00 (s, 1, ), (m, 8, Ar-), 6.89 (s, 1, 4-C), 4.12 (s, 2, C 5 C 2 ), 2.75 (s, 3, -C 3 ). (VIIIc) PMR (CDCl 3 DMO) : (m, 8, Ar- & -), (s, 2, O-C 2 -O), 5.92 (s, 1, 4-C), 3.99 (s, 2, C 5 C 2 ), (s, 3, -C 3 ). Mass fragments (m/z): 336M, 335, 320, 263, 246, 222, 207, 178, 129, 114, 90. (VIIIf) PMR (CDCl 3 DMO) : 127
12 8.89 (s, 1, -), (m, 7, Ar-), 6.08 (s, 1, 4-C), (d, 1 of C 5 C 2 ), (d, 1 of C 5 C 2 ), 1.24 (s, 3, -C 3 ). YTEI OF 2-(ETYLTIO)-4-ARYL-4,5-DIYDRO-1- IDEO[1,2-d]PYRIMIDIE General Procedure Indeno[1,2-d]pyrimidine-2-thione (0.004 mole) was dissolved in ethanol. To it, added ao solution, which was prepared by dissolving ao (0.004 mole, 0.16 g) in water (2 ml). The mixture was cooled. To this mixture, diethyl sulphate (0.6 ml, mole) was added drop wise while stirring the mixture continuously. The reaction mixture was refluxed for 3 hours. The reaction was monitored by thin layer chromatography (TLC) using silica gel-g plates. Ethyl acetate and n-hexane mixture was used as eluting solvents (1:1) and after drying, the plates were exposed to iodine chamber. The reaction mixture was cooled and poured over crushed ice. olid separated was filtered under reduced pressure, washed with ethanol and dried. It was recrystallised from ethanol to provide a pure sample of the product. A typical procedure is given below: 128
13 VIIIg 2-(ethylthio)-4-(4-methoxyphenyl)-4,5-dihydro-1indeno[1,2-d]pyrimidines 4-(4-methoxyphenyl)-1,3,4,5-tetrahydro-2-indeno[1,2-d] pyrimidine-2-thione (0.004 mole, g) was dissolved in ethanol. To it, added ao solution, which was pepared by dissolving ao (0.004 mole, 0.16 g) in water (2 ml). The mixture was cooled. To this mixture, diethyl sulphate (0.6 ml, mole) was added drop wise while stirring the mixture continuously. The reaction mixture was refluxed for 3 hours. The reaction was monitored by thin layer chromatography (TLC) using silica gel-g plates. Ethyl acetate and n-hexane mixture was used as eluting solvents (1:1) and after drying, the plates were exposed to iodine chamber. The mixture was cooled and poured over crushed ice. olid separated was filtered under reduced pressure, washed with ethanol and dried. It was recrystallized from ethanol to provide a pure sample of the product. M.P. = C Yield = 79-87%. PMR (CDCl 3 DMO) : (m, 9, Ar- & -), 5.83 (s, 1, 4-C), 3.94( s, 2, C 5 C 2 ), 3.86(s, 3, OC 3 ), ( q, 1 of -C 2 ), (q, 1 of - C 2 ), (t, 3, -C 2 -C 3 ). 129
14 IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), (C --- C), (C-). Mass fragments (m/z): 336 M, 335, 334, 249, 219, 178, 140, 129. (VIIIh) PMR (CDCl 3 DMO) : 9.00 (s, 1, ), (m, 8, Ar-), 5.75 (s, 1, 4-C), 4.12 ( s, 2, C 5 C 2 ), ( q, 2, -C 2 ), (t, 3, -C 2 - C 3 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), & (O 2 ), (C --- C), (C-). Mass fragments (m/z): 264, 216, 155, 135, 90, 77. (VIIIi) PMR (CDCl 3 DMO) : (m, 8, Ar- & -), (s, 2, O-C 2 -O), 5.92 (s, 1, 4-C), 3.98 ( s, 2, C 5 C 2 ), (q, 1 of -C 2 ), ( q, 1 of -C 2 ), (t, 3, -C 2 -C 3 ). 130
15 IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), ( C --- C), (C-). (VIIIj) PMR (CDCl 3 DMO) : 8.17 (s, 1, -), (m, 7, Ar- ), 8.01(s, 1, O), 5.92 (s, 1, 4), 4.14 ( s, 2, C 5 C 2 ), 3.98 (s, 3, OC 3 ), (q, 1 of -C 2 ), ( q, 1 of -C 2 ), (t, 3, -C 2 - C 3 ). IR (KBr, cm -1 ): (O- str.), (- str.), (C- str.), (C=C str.), (C --- C), (C-). (VIIIl) PMR (CDCl 3 DMO) : 8.91 (s, 1, -), (m, 7, Ar- ), 6.08 (s, 1, 4), (q, 2, -C 2 ), (d, 1 of C 5 C 2 ), (d, 1 of C 5 C 2 ), (t, 3, -C 2 -C 3 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), ( C --- C), (C-). 131
16 (VIIIm) PMR (CDCl 3 DMO) : 8.17 (s, 1, -), (m, 9, Ar- ), 5.30 (s, 1, 4), 4.13 (s, 2, C 5 C 2 ), (q, 2, -C 2 ), (t, 3, -C 2 - C 3 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), ( C --- C), (C-). Mass fragments (m/z): 305, 290, 276, 244,230, 219, 218, 216, 191,178, 128,114, 90, 77. YTEI OF 2-(BEZYLTIO)-4-ARYL-4,5-DIYDRO-1- IDEO[1,2-d]PYRIMIDIE General Procedure Indeno[1,2-d]pyrimidine-2-thiones (0.004 mole) were dissolved in alcohol (2-3 ml). The solution was diluted with water (2 ml). To it, benzyl chloride (0.5 ml, mole) was added and the mixture was refluxed for 5 hours. The reaction was monitored by thin layer chromatography (TLC) using silica gel-g plates. Ethyl acetate and n-hexane mixture was used as eluting solvents (1:1) and after drying, the plates were exposed to iodine chamber. The reaction mixture was cooled and poured over crushed ice. 132
17 olid separated was filtered under reduced pressure, washed with ethanol and dried. It was recrystallized from ethanol to provide a pure sample of the product. A typical procedure is given below: VIIIn 2-(benzylthio)-4-(4-methoxyphenyl)-4,5-dihydro-1- indeno[1,2-d]pyrimidines 4-(4-methoxyphenyl)-1,3,4,5-tetrahydro-2-indeno[1,2- d]pyrimidine-2-thione (0.004 mole, g) was dissolved in alcohol (2-3 ml). The solution was diluted with water (2 ml). To it, benzyl chloride (0.5 ml, mole) was added and the mixture was refluxed for 5 hours. The reaction was monitored by thin layer chromatography (TLC) using silica gel-g plates. Ethyl acetate and n-hexane mixture was used as eluting solvents (1:1) and after drying, the plates were exposed to iodine chamber. The reaction mixture was cooled and poured over crushed ice. olid separated was filtered under reduced pressure, washed with ethanol and dried. It was recrystallized from ethanol to provide a pure sample of the product. M.P. = C Yield = 29% 133
18 PMR (CDCl 3 DMO) : (m, 14, & Ar-), 5.97 (s, 1, 4-C), 4.60 ( d, 1 of - C 2 ), 4.12 ( d, 1 of -C 2 ), 4.01 (s, 2, C 5 C 2 ), 3.86 ( s, 3, OC 3 ). Mass fragments (m/z): 398 M, 396, 365, 320, 308, 307, 273, 249, 219, 175, 149, 132, 91, 90. (VIIIo) PMR (CDCl 3 DMO) : 8.96 (s, 1, ), (m, 13, Ar-), 6.13 (s, 1, 4-C), ( d, 1 of -C 2 ), ( d, 1 of -C 2 ), 4.15 (s, 2, C 5 C 2 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), & (O 2 ), (C --- C), (C-). (VIIIp) PMR (CDCl 3 DMO) : (m, 13, Ar- & -), 6.02 (s, 2, O-C 2 -O), 5.93 (s, 1, 4-C), 3.97 (s, 2, C 5 C 2 ), 4.58 ( d, 1 of -C 2 ), 4.06 ( d, 1 of -C 2 ). IR (KBr, cm -1 ): 134
19 (- str.), (C- str.), (C=C str.), ( C --- C), (C-). YTEI OF 2-(BUTYLTIO)-4-ARYL-4,5-DIYDRO-1- IDEO[1,2-d]PYRIMIDIE General Procedure A mixture of powdered Indeno[1,2-d]pyrimidine-2-thiones ( mole), butyl bromide (0.004 mole) and absolute alcohol (2ml) was taken in round bottom flask ( 100 ml) and was refluxed for 5 hours. The reaction was monitored by thin layer chromatography (TLC) using silica gel-g plates. Ethyl acetate and n-hexane mixture was used as eluting solvents (1:1) and after drying, the plates were exposed to iodine chamber. After refluxing, the reaction mixture was transferred to 100 ml beaker. It was allowed to stand at room temperature for hours. The product separated after continuous scratching with the glass rod. It was filtered under reduced pressure and washed with alcohol and dried. The product was recrystallized from ethanol. A typical procedure is given below: (VIIIt) 2-(butylthio)-4-(4-methoxyphenyl)-4,5-dihydro-1- indeno[1,2-d]pyrimidines 135
20 A mixture of powdered 4-(4-methoxyphenyl)-1,3,4,5-tetrahydro-2indeno[1,2-d]pyrimidine-2-thione (0.004 mole, g), butyl bromide (0.004 mole) and absolute alcohol ( 2ml) was taken in round bottom flask ( 100 ml) and was refluxed for 5 hours. The reaction was monitored by thin layer chromatography (TLC) using silica gel-g plates. Ethyl acetate and n- hexane mixture was used as eluting solvents (1:1) and after drying, the plates were exposed to iodine chamber. After refluxing the reaction mixture was transferred to 100 ml beaker. After a long standing for hrs., the product separated was filtered under reduced pressure and washed with alcohol and dried. Then, the product was recrystallized from ethanol. M.P. = C Yield = 56.49% PMR (CDCl 3 DMO) : (m, 9, & Ar-), 5.76 (s, 1, 4-C), 4.10 (s, 2, C 5 C 2 ), 3.89 (s, 3, OC 3 ), (t, 2, -C 2 -C 2 -C 2 -C 3 ), ( m, 4, -C 2 -C 2 -C 2 -C 3 ), (t, 3, -C 2 -C 2 -C 2 -C 3 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), (C --- C), (C-). 136
21 Mass fragments (m/z): 364 M, 363, 329, 249, 178. (VIIIu) PMR (CDCl 3 DMO) : (m, 8, Ar- & -), (s, 2, O-C 2 -O), 5.98 (s, 1, 4-C), 3.98 (s, 2, C 5 C 2 ), (t, 2, -C 2 -C 2 - C 2 -C 3 ), ( m, 2, -C 2 -C 2 -C 2 -C 3 ), (m, 2, -C 2 -C 2 -C 2 -C 3 ), (t, 3, -C 2 -C 2 -C 2 -C 3 ). IR (KBr, cm -1 ): (- str.), (C- str.), (C=C str.), ( C --- C), (C-). Mass fragments (m/z): 265, 250, 245, 168, 129, 115, 114, 90, 89, 65. (C 3 ) 2 O 4 X R (C 2 5 ) 2 O 4 n - C 4 9 Br C 2 C 6 5 Cl R VIIa-j VIIIa-z 137
22 TABLE 7 CARACTERIZATIO DATA OF PRODUCT (VIIIa-VIIIz):. o. Product R X Reagent Time (hrs.) M.P. ( 0 C) Yield (%) 1. VIIIa 4-OC 3 -C 3 Dimethyl ulphate VIIIb 3-O 2 -C 3 Dimethyl ulphate 3. VIIIc 2,3-(O-C 2 -O) -C 3 Dimethyl ulphate 4. VIIId 4-O,3-OC 3 -C 3 Dimethyl ulphate 5. VIIIe 4-O 2 -C 3 Dimethyl ulphate 6. VIIIf 2,4-(Cl) -C 3 Dimethyl ulphate 7. VIIIg 4-OC 3 -C 2 5 Diethyl ulphate 8. VIIIh 3-O 2 -C 2 5 Diethyl ulphate 9. VIIIi 2,3-(O-C 2 -O) -C 2 5 Diethyl ulphate 10. VIIIj 4-O,3-OC 3 -C 2 5 Diethyl ulphate 11. VIIIk 4-O 2 -C 2 5 Diethyl ulphate
23 12. VIIIl 2,4-(Cl) -C 2 5 Diethyl ulphate 13. VIIIm -C 2 5 Diethyl ulphate 14. VIIIn 4-OC 3 -C 2 Benzyl C 6 5 Chloride 15. VIIIo 3-O 2 -C 2 Benzyl C 6 5 Chloride 16. VIIIp 2,3-(O-C 2 -O) -C 2 Benzyl C 6 5 Chloride VIIIq 4-O,3-OC 3 -C 2 Benzyl C 6 5 Chloride VIIIr 2-O 2 -C 2 C 6 5 Benzyl Chloride 20. VIIIs 4-OC 3 -C 4 9 Butyl bromide 21. VIIIt 3-O 2 -C 4 9 Butyl bromide 22. VIIIu 2,3-(O-C 2 -O) -C 4 9 Butyl bromide 23. VIIIv 4-O,3-OC 3 -C 4 9 Butyl bromide 24. VIIIw 4-O 2 -C 4 9 Butyl bromide 25. VIIIx 2-O 2 -C 4 9 Butyl bromide
24 26. VIIIy -C 4 9 Butyl bromide ote: All the above compounds were recrystallized from ethanol. 140
25 REULT AD DICUIO ifedipine and its related derivatives which have appeared commercially have one asymmetric centre at C4 if the ester functions are varied at position 3 & 5. The second important aspect for its activity is the boat shaped conformation of the dihydropyridine ring. This aspect is the most important factor in its activity as calcium channel blocker. R 2 R 1 OOC COOR 3 3 C C 3 ifedipine: R 1 = -C 3, R 2 = 2-O 2, R 3 = -C 3 itrendipine : R 1 = - C 3, R 2 = 3-O 2, R 3 = -C 2 C 3 icardipine : R 1 = -C 2 C 2 (C 3 )Bu, R 2 = 3-O 2, R 3 = -C 2 5 Considering these aspects, instead of varying the ester functions, we thought of introducing nitrogen at one of the position C3. Thus, creating the optical activity at C4. It was the thought of preparing such systems and looking back at literature Biginelli had already prepared such systems by acid catalysed condensation of acetoacetic ester, urea & aromatic aldehyde. In line with this, besides substituting thiourea, we introduced cyclic ketone 141
26 viz. 1-indanone as active methylene compound. During the past decade a number of publications and reviews have advocated the advantages of microwave irradiations to carry out organic synthesis. o MORE technique was used for improving the results. The acid catalysed condensation of aromatic aldehyde, 1-indanone & thiourea was carried out in open borosil glass beaker. Ethanol was used as energy transfer medium & reaction mixture was irradiated in domestic microwave oven for minutes. The reaction conditions were optimized. The reaction was followed by thin layer chromatography (TLC) and it was found that maximum yields were obtained at 30% microwave power level. The same reaction was also carried out through thermal heating and it took approx. 5 to 6 hours to complete the reaction. The results have shown that through microwave heating, there is reduction in time, enhancement in the yields and besides this cleaner products are formed i.e. side products are minimized and therefore work-up of the reaction mixture becomes easier. The details about the synthetic procedure are given under experimental section. In most of the cases, the product separated out on keeping the reaction mixture at room temperature for 3-4 hours. 142
27 Other compounds (VIIb VIIj) were also synthesized similarly and are listed in Table 6 along with their characterization data. O CO 2 R 2 C 30 % w Conc. Cl abs. alcohol R VIIa-j TABLE 6 CARACTERIZATIO DATA OF PRODUCT (VIIa VIIj):. o Compd R Reaction time % Yield a M.P. Micro wave Time (min) Reflux Time (hrs) Micro wave Reflux ( 0 C) VIIa 4-OC VIIb 3-O VIIc 2,3-(O-C 2 -O) VIId 4-O,3-OC VIIe 4-O
28 5 247 VIIf 2-C VIIg 2,4-(Cl) VIIh 2-O VIIi VIIj 4-(C 3 ) a Yield of crude product As a case in illustration, compound VIIa was synthesized by taking 4-methoxy benzaldehyde, 1-indanone & thiourea dissolved in absolute alcohol to which catalytic amount of conc. hydrochloric acid was added in a open borosil glass beaker. The reaction mixture was irradiated at 30% microwave power level for 8.00 minutes. The progress of reaction was followed by TLC. The reaction mixture was allowed to stand at room temperature for 5.00 hours and 30 minutes. The product separated was filtered, washed with alcohol and recrystallized out of ethanol. The product had a sharp melting point at C and it was obtained in 52 % yield. The PMR spectra of compound VIIa (Plate 21) showed a characteristic singlet at 5.66 due to 4-C proton. The singlet at
29 and 8.26 were assigned to 1 & 3 protons which got exchanged with D 2 O. A multiplet due to eight protons were observed at A broad singlet was obtained at due to 5-C 2 protons. And a singlet at 3.88 was due to 4-OC 3. IR spectra of compound VIIa (Plate 22) exhibit band for secondary - stretching at cm -1, C- stretching at & cm -1 and C=C stretching vib. at cm -1. Mass spectra of compound VIIa (Plate 23) showed the M peak at m/z 308, M1 peak at m/z 309 and other important peaks at m/z 307, 249, 178, 129, 120. Thus, all the spectral data support the assigned structure VIIa. OC 3 VIIa 145
30 The fragmentation pattern of this compound (VIIa) is given below (Plate 23):. -. m/z = 129 OC 3 m/z = 308 m/z = 307 OC 3 C C 2 C OC 3. m/z = 178 m/z = 249 OC 3 m/z = 129 C OC 3. m/z = 178. C. m/z = 188 OC 3 m/z =
31 A possible fragmentation pattern for the compound VIIi is given below (Plate 24):.. C m/z = 59 m/z = 278 m/z = 219 (12.6%)... m/z = 77 m/z = 201 (9.74%) (91.8%).. C C. m/z = 188 (7.89%). C m/z = 129 m/z = 149 m/z = 90 (1.03%) (1.85%). C. m/z = 173 (2.97%) m/z = 105 (2.77%). C (1.74%) m/z = 114 (18.81%) 147
32 The second aspect of these derivatives was to convert the pyrimidine ring into dihydropyrimidine system. As dihydropyrimidines are commonly proposed to adopt a boat shaped conformation to bind itself to the receptor site. The stereochemical relationship between the aryl group and the dihydropyrimidine ring was found to be one of the factors having pronounced effect on the biological activity. These thiones were converted to their enol derivatives. X A R (C 3 ) 2 O 4 (C 2 5 ) 2 O 4 n - C 4 9 Br C 2 C 6 5 Cl A R VIIa-j VIIIa-y The thiones were converted to their thio ethers where X was -C 3, - C 2 5, - C 2 (C 2 ) 2 C 3 & -C 2 C 6 5. In these cases, thiones was treated with dimethyl sulphate, diethyl sulphate, butyl bromide and benzyl chloride respectively as explained in the experimental section. 148
33 TABLE 7 CARACTERIZATIO DATA OF PRODUCT (VIIIa-VIIIz):. o. Product R X Reagent Time (hrs.) M.P. ( 0 C) Yield (%) 1. VIIIa 4-OC 3 -C 3 Dimethyl ulphate VIIIb 3-O 2 -C 3 Dimethyl ulphate 3. VIIIc 2,3-(O-C 2 -O) -C 3 Dimethyl ulphate 4. VIIId 4-O,3-OC 3 -C 3 Dimethyl ulphate 5. VIIIe 4-O 2 -C 3 Dimethyl ulphate 6. VIIIf 2,4-(Cl) -C 3 Dimethyl ulphate 7. VIIIg 4-OC 3 -C 2 5 Diethyl ulphate 8. VIIIh 3-O 2 -C 2 5 Diethyl ulphate 9. VIIIi 2,3-(O-C 2 -O) -C 2 5 Diethyl ulphate 10. VIIIj 4-O,3-OC 3 -C 2 5 Diethyl ulphate 11. VIIIk 4-O 2 -C 2 5 Diethyl ulphate
34 12. VIIIl 2,4-(Cl) -C 2 5 Diethyl ulphate 13. VIIIm -C 2 5 Diethyl ulphate 14. VIIIn 4-OC 3 -C 2 Benzyl C 6 5 Chloride 15. VIIIo 3-O 2 -C 2 Benzyl C 6 5 Chloride 16. VIIIp 2,3-(O-C 2 -O) -C 2 Benzyl C 6 5 Chloride VIIIq 4-O,3-OC 3 -C 2 Benzyl C 6 5 Chloride VIIIr 2-O 2 -C 2 C 6 5 Benzyl Chloride 20. VIIIs 4-OC 3 -C 4 9 Butyl bromide 21. VIIIt 3-O 2 -C 4 9 Butyl bromide 22. VIIIu 2,3-(O-C 2 -O) -C 4 9 Butyl bromide 23. VIIIv 4-O,3-OC 3 -C 4 9 Butyl bromide 24. VIIIw 4-O 2 -C 4 9 Butyl bromide 25. VIIIx 2-O 2 -C 4 9 Butyl bromide
35 26. VIIIy -C 4 9 Butyl bromide The ultraviolet spectra of -methyl, -ethyl, -butyl and -benzyl did not show any bathochromic shift which would have been possible if the two double bonds in pyrimidine ring got conjugated in the preparation of these derivatives. Thus, the structure VIIIa-VIIIy for two double bonds is suggested. Further, conformation of the total structure was done through PMR, IR and Mass spectral data which is completely in line with the fragmentation of -derivatives. In case of compound VIIIa (Plate 25), the PMR spectrum showed a characteristic singlet at 5.35 due to 4-C proton and a two proton singlet at 2.1due to C 5 -C 2. A multiplet was observed at due to eight aromatic protons and 1 proton. And a singlet at 3.89 was due to 4-OC 3. Also a singlet was obtained at 2.72 due to -C 3 protons. Thus, the PMR spectra of VIIIa (Plate 25) showed a characteristic difference when compared with PMR spectra of VIIa (Plate 21). The obvious and expected difference in PMR spectra was due to -methyl group. Mass spectra of compound VIIIa (Plate 26) showed the M peak at m/z 322, M1 peak at m/z 323 and other important peaks at m/z 321, 320, 289, 274, 155,
36 A possible fragmentation pattern for the compound VIIIa is given below (Plate 26): C 3. C 3 OC 3 OC 3 m/z = C 3 C C 3 m/z = 321 OC 3 m/z = OC 3 C 3 m/z = 155 OC 3 - C 3. - C 3. m/z = 289 m/z = 274 OC 3 - CO m/z = 129 m/z = 178 OC 3 m/z = 167 m/z =
37 A possible fragmentation pattern for the compound VIIIg is given below (Plate 28): C 2 C 3. C 2 C 3 -. OC 3 OC 3 m/z = 336 m/z = C 2 C. C 2 C 3 OC 3 OC 3 m/z = 87 m/z = 249 m/z = CO. 3 C 2 C m/z = 140 OC 3 m/z = 219. C 2 C 3 m/z = 129 OC 3 m/z =
38 A possible fragmentation pattern for the compound VIIIn is given below (Plate 29): C 2 C C 2 C 6 5 C 2 m/z = 398 OC 3 m/z = 90 m/z = C 2 C 6 5 OC 3 C -. m/z = 396 OC 3 C 2 C 6 5 m/z = 149 OC 3 - C 2 C 6 5 m/z = OC 3 m/z = CO m/z = 273 OC 3 C 2 C 6 5 m/z = 365 m/z = C 6 2 C C C 2 m/z = 320 OC 3 C 2 C C 6 2 C m/z = 307 OC 3 m/z = 91 C 2. m/z = 77 m/z = 175 C C OC 3 m/z =
39 A possible fragmentation pattern for the compound VIIIs is given below (Plate 31): C 4 9 C OC 3 m/z = 364 OC 3 m/z = C 4 9 m/z = OC 3 OC 3 C 4 9 C C 4 9. m/z = 275 m/z = 331 m/z = 249. m/z = 129 OC 3 m/z =
40 A possible fragmentation pattern for the compound VIIIm is given below (Plate 32):.. C 2 5 C m/z = 306 m/z = C C 2 5. m/z = 61. m/z = 77 (32%) C m/z = 276 (100%) m/z = C 2 =C 2 m/z = 244 (45.4%).. m/z = 202 (10%) C C 2 5 m/z = 219 (50%). m/z = 87 (11%) 156
Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction
Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction P. Veeraraghavan Ramachandran* and Prem B. Chanda Department of Chemistry, Purdue
More informationZinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to α- Ketoamides
Supporting information for Zinc Chloride Promoted Formal xidative Coupling of Aromatic Aldehydes and Isocyanides to α- Ketoamides Marinus Bouma, Géraldine Masson* and Jieping Zhu* Institut de Chimie des
More informationElectronic Supplementary Information (ESI)
Electronic Supplementary Information (ESI) Mild and convenient one-pot synthesis of 2-amino-1,3,4-oxadiazoles promoted by trimethylsilyl isothiocyanate (TMSNCS) Dinneswara Reddy Guda, Hyeon Mo Cho, Myong
More information2 - chloro phenothiazine was prepared by the method of knoevenagal (loc. cit); (1914). 2-Chloro-10-chloroacetyl phenothiazine (1): To a solution of
103 104 SCHEME II SOME NEW SUBSTITUTED BENZYLIDENE AMINOTHIAZOL / OXAZOL PHENOTHIAZINES; SUBSTITUTED AZETIDINYL THIAZOL/ OXAZOL PHENOTHIAZINES HAVE BEEN SYNTHESIZED AS SHOWN IN SCHEME-II, INVOLVES THE
More information3016 Oxidation of ricinoleic acid (from castor oil) with KMnO 4 to azelaic acid
6 Oxidation of ricinoleic acid (from castor oil) with KMnO 4 to azelaic acid CH -(CH ) OH (CH ) -COOH KMnO 4 /KOH HOOC-(CH ) -COOH C H 4 O (.) KMnO 4 KOH (.) (6.) C H 6 O 4 (.) Classification Reaction
More informationRameshwar Prasad Pandit and Yong Rok Lee * School of Chemical Engineering, Yeungnam University, Gyeongsan , Korea
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Novel ne-pot Synthesis of Diverse γ,δ-unsaturated β-ketoesters by Thermal
More informationPreparation, isolation and characterization of N α -Fmoc-peptide isocyanates: Solution synthesis of oligo-α-peptidyl ureas
SUPPORTING INFORMATION Preparation, isolation and characterization of N α -Fmoc-peptide isocyanates: Solution synthesis of oligo-α-peptidyl ureas Vommina V. Suresh Babu*, Basanagoud S. Patil, and Rao Venkataramanarao
More informationMasatoshi Shibuya,Takahisa Sato, Masaki Tomizawa, and Yoshiharu Iwabuchi* Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences,
Oxoammonium ion/naclo 2 : An Expedient, Catalytic System for One-pot Oxidation of Primary Alcohols to Carboxylic Acid with Broad Substrate Applicability Masatoshi Shibuya,Takahisa Sato, Masaki Tomizawa,
More informationSupporting Information
Supporting Information Synthesis of N-Heteropolycyclic Compounds Including Quinazolinone Skeletons by Using Friedel-Crafts Alkylation Bu Keun Oh, Eun Bi Ko, Jin Wook Han* and Chang Ho Oh* Department of
More informationAllenylphosphine oxides as simple scaffolds for. phosphinoylindoles and phosphinoylisocoumarins
Supporting Information for Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins G. Gangadhararao, Ramesh Kotikalapudi, M. Nagarjuna Reddy and K. C. Kumara Swamy*
More informationThe First Au-Nanoparticles Catalyzed Green Synthesis of Propargylamines Via Three-Component Coupling Reaction of Aldehyde, Alkyne And Amine
Supporting information of The First Au-anoparticles Catalyzed Green Synthesis of Propargylamines Via Three-Component Coupling Reaction of Aldehyde, Alkyne And Amine Mazaahir Kidwai a *, Vikas Bansal a,
More informationSupplemental Information. Reactivity of Monovinyl (Meth)Acrylates Containing Cyclic Carbonates
Supplemental Information Reactivity of Monovinyl (Meth)Acrylates Containing Cyclic Carbonates Kathryn A. Berchtold a, Jun Nie b, Jeffrey W. Stansbury c, d, and Christopher N. Bowman c, d, a Materials Science
More informationA Novel Synthesis of Arylpyrrolo[1,2-a]pyrazinone Derivatives
Molecules 2004, 9, 574-582 molecules ISS 1420-049 http://www.mdpi.org A ovel Synthesis of ylpyrrolo[1,2-a]pyrazinone Derivatives Fei Wang*, Jiawei Wang and Shoufang Zhang School of Pharmaceutical Engineering,
More informationSupporting Materials. Experimental Section. internal standard TMS (0 ppm). The peak patterns are indicated as follows: s, singlet; d,
CuBr-Catalyzed Efficient Alkynylation of sp 3 C-H Bonds Adjacent to a itrogen Atom Zhiping Li and Chao-Jun Li* Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec H3A
More informationSynthesis of Some Novel 2,4-Thiazolidinedione Derivatives and Their Biological Screening as Antidiabetic Agents
Asian Journal of Chemistry Vol. 21, No. 7 (2009), 5068-5072 ynthesis of ome Novel 2,4-Thiazolidinedione Derivatives and Their Biological creening as Antidiabetic Agents.K. JIWANE*, V.K. INGH, K.P. NAMDE
More informationSynthesis and Blastocyst Implantation Inhibition Potential of Lupeol Derivatives in Female Mice
Supporting Information Rec. Nat. Prod. 9:4 (2015) 561-566 Synthesis and Blastocyst Implantation Inhibition Potential of Lupeol Derivatives in Female Mice Anita Mahapatra 1*, Purvi Shah 1, Mehul Jivrajani
More informationThermal shift binding experiments were carried out using Thermofluor 384 ELS system. Protein
Supplementary Methods Thermal shift assays Thermal shift binding experiments were carried out using Thermofluor 384 ELS system. Protein unfolding was examined by monitoring the fluorescence of ANS (1-anilinonaphthalene-8-
More informationSupporting Information. Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base
Supporting Information Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base Feng Wang, a Haijun Yang, b Hua Fu, b,c * and Zhichao Pei a * a College
More information12BL Experiment 2: Extraction & Saponification of Trimyristin from Nutmeg
12BL Experiment 2: Extraction & Saponification of Trimyristin from Nutmeg Safety: Proper lab goggles/glasses must be worn (even over prescription glasses). Heating of organic solvents releases irritating
More informationSupporting Information
Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2016 Supporting Information Fangyi Li, Changgui Zhao, and Jian Wang* Department of Pharmacology
More informationDivergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes
Divergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes Serena Mantenuto, Fabio Mantellini, Gianfranco Favi,* and Orazio A. Attanasi Department of Biomolecular
More informationp-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of
Supporting Information for: p-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN 3 for Synthesis of 4-Aryl-NH-1,2,3-triazoles Xue-Jing Quan, Zhi-Hui Ren, Yao-Yu Wang, and
More informationSupporting Information for. Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of. 3,5-Disubstituted Pyridines: Mechanistic Studies
Supporting Information for Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of 3,5-Disubstituted Pyridines: Mechanistic Studies Ta-Hsien Chuang* a, Yu-Chi Chen b and Someshwar Pola
More informationCopper(II) Ionic Liquid Catalyzed Cyclization-Aromatization of. Hydrazones with Dimethyl Acetylenedicarboxylate: A Green Synthesis
Copper(II) Ionic Liquid Catalyzed Cyclization-Aromatization of Hydrazones with Dimethyl Acetylenedicarboxylate: A Green Synthesis of Fully Substituted Pyrazoles Shirin Safaei, Iraj Mohammadpoor-Baltork,*
More informationSupporting Information. for. Access to pyrrolo-pyridines by gold-catalyzed. hydroarylation of pyrroles tethered to terminal alkynes
Supporting Information for Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes Elena Borsini 1, Gianluigi Broggini* 1, Andrea Fasana 1, Chiara Baldassarri
More informationSupplementary Materials Contents
Supplementary Materials Contents Supporting information... S1 1. General Information & Materials... S2 2. General Procedure for ptimization of Amidation of Aryl Bromides with Copper/,-Dimethylglycine Catalytic
More informationSupporting Information. for. Pd-catalyzed decarboxylative Heck vinylation of. 2-nitro-benzoates in the presence of CuF 2
Supporting Information for Pd-catalyzed decarboxylative Heck vinylation of 2-nitro-benzoates in the presence of CuF 2 Lukas J. Gooßen*, Bettina Zimmermann, Thomas Knauber Address: Department of Chemistry,
More informationSchwartz s reagent-mediated regiospecific synthesis of 2,3-disubstituted indoles from isatins
Electronic Supplementary Information (ESI) Schwartz s reagent-mediated regiospecific synthesis of 2,3-disubstituted indoles from isatins A. Ulikowski and B. Furman* Institute of Organic Chemistry, Polish
More informationSupporting Information
Supporting Information [Cp*IrCl 2 ] 2 catalysed indirect functionalisation of alcohols: ovel strategies for the synthesis of substituted indoles Simon Whitney, Ronald Grigg *, Andrew Derrick and Ann Keep
More informationUse of degradable cationic surfactants with cleavable linkages for enhancing the. chemiluminescence of acridinium ester labels. Supplementary Material
Use of degradable cationic surfactants with cleavable linkages for enhancing the chemiluminescence of acridinium ester labels Supplementary Material Anand atrajan*and David Wen Siemens Healthcare Diagnostics
More informationSynthesis and Antimicrobial Evaluation of some 2-Azetidinone derivatives
International Journal of ChemTech Research CDE( USA): IJCRGG ISS : 0974-4290 Vol.1, o.2, pp 153-157, April-June 2009 Synthesis and Antimicrobial Evaluation of some 2-Azetidinone derivatives S.Jubie*, B.Gowramma,
More informationSupporting Information. Radical fluorination powered expedient synthesis of 3 fluorobicyclo[1.1.1]pentan 1 amine
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Radical fluorination powered expedient synthesis
More informationSupporting Information for. Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the. analysis of Glucose in Whole Blood
Supporting Information for Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the analysis of Glucose in Whole Blood Yueling Liu, Jingwei Zhu, Yanmei Xu, Yu Qin*, Dechen Jiang*
More informationPyridazine N-Oxides as Precursors of Metallocarbenes: Rhodium-Catalyzed Transannulation with Pyrroles. Supporting Information
Pyridazine N-Oxides as Precursors of Metallocarbenes: Rhodium-Catalyzed Transannulation with Pyrroles Vinaykumar Kanchupalli, Desna Joseph and Sreenivas Katukojvala* Department of Chemistry, Indian Institute
More informationStereoselective Aza-Darzens Reactions of Tert- Butanesulfinimines: Convenient Access to Chiral Aziridines
Stereoselective Aza-Darzens Reactions of Tert- Butanesulfinimines: Convenient Access to Chiral Aziridines Toni Moragas Solá, a Ian Churcher, b William Lewis a and Robert A. Stockman* a Supplementary Information
More informationEthyl 2-hydroxy-4-methyl-1-((prop-2-yn-1-yloxy)methyl)cyclohex-3-enecarboxylate (16):
General methods: 1 H NMR and 13 C NMR spectra were recorded in CDCl 3 or CDCl3 and CCl 4 as solvent on 300 MHz or 500 MHz spectrometer at ambient temperature. The coupling constant J is given in Hz. The
More informationRegioective Halogenation of 2-Substituted-1,2,3-Triazole via sp 2 C-H Activation
Regioective Halogenation of 2-Substituted-1,2,3-Triazole via sp 2 C-H Activation Qingshan Tian, Xianmin Chen, Wei Liu, Zechao Wang, Suping Shi, Chunxiang Kuang,* Department of Chemistry, Tongji University,
More informationSupporting Information
Supporting Information Unconventional Passerini Reaction towards α-aminoxyamides Ajay L. Chandgude, Alexander Dömling* Department of Drug Design, University of Groningen, Antonius Deusinglaan 1, 9713 AV
More informationPreparation of Stable Aziridinium Ions and Their Ring Openings
Supplementary Information Preparation of Stable Aziridinium Ions and Their Ring Openings Yongeun Kim a Hyun-Joon Ha*, a Sae Young Yun b and Won Koo Lee,*,b a Department of Chemistry and Protein Research
More information1,5-Electrocyclization of conjugated azomethine ylides derived from 3-formyl chromene and N-alkyl amino acids/esters
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 7 Supporting Information for,5-electrocyclization of conjugated azomethine ylides
More informationChemo- and Enantioselective Rh-Catalyzed Hydrogenation of 3-Methylene-1,2-diazetidines: Application to Vicinal Diamine Synthesis
Chemo- and Enantioselective Rh-Catalyzed Hydrogenation of 3-Methylene-1,2-diazetidines: Application to Vicinal Diamine Synthesis Greg P. Iacobini, a David W. Porter, b and Michael Shipman* a a Department
More informationLewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines
Supporting Information for Lewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines Yingle Liu a, Jiawang Liu
More informationImproved Carbonylation of Heterocyclic Chlorides and Challenging Aryl Bromides
Albaneze-Walker et al S-1 Improved Carbonylation of Heterocyclic Chlorides and Challenging Aryl Bromides Jennifer Albaneze-Walker*, Charles Bazaral, Tanya Leavey, Peter G. Dormer, and Jerry A. Murry Department
More information4.2 Aims and Objectives
4.1 Introduction The reaction between the products of interaction of halogens and silver salts of carboxylic acids and olefns forms the basis of the Woodward and Prevost methods of cis- and trans- hydroxylations
More informationManganese powder promoted highly efficient and selective synthesis of fullerene mono- and biscycloadducts at room temperature
Supplementary Information Manganese powder promoted highly efficient and selective synthesis of fullerene mono- and biscycloadducts at room temperature Weili Si 1, Xuan Zhang 1, Shirong Lu 1, Takeshi Yasuda
More informationBase-promoted acetal formation employing aryl salicylates
Base-promoted acetal formation employing aryl salicylates Pinmanee Boontheung, Patrick Perlmutter*, and Evaloni Puniani School of Chemistry, Monash University, PO Box 23, Victoria 3800 Australia E-mail:
More informationSynthesis and biological activities of some 3,5-disubstituted-Δ²-pyrazoline derivatives
Oriental Journal of Chemistry Vol. 24(2), 607-612 (2008) Synthesis and biological activities of some 3,5-disubstituted-Δ²-pyrazoline derivatives SADAF J.GILANI, SUROOR A. KHAN*, OZAIR ALAM and HARISH KUMAR
More informationSynthesis of Some New 4,5-Substituted-4H-1,2,4-triazole-3-thiol Derivatives
Molecules 2004, 9, 204-212 molecules ISS 1420-3049 http://www.mdpi.org Synthesis of Some ew 4,5-Substituted-4-1,2,4-triazole-3-thiol Derivatives A. Cansız, M. Koparır * and A. Demirdağ Department of Chemistry,
More informationContinuous flow retro-diels Alder reaction: an. efficient method for the preparation of pyrimidinone
Supporting Information for Continuous flow retro-diels Alder reaction: an efficient method for the preparation of pyrimidinone derivatives Imane Nekkaa 1, Márta Palkó 1, István M. Mándity 1, and Ferenc
More informationApplication of Green Chemistry Principle in Synthesis of Phenytoin and Its Biogical Evaluation as Anticonvulsant Agents
http://www.e-journals.net ISSN: 0973-4945; CODEN ECJHAO E- Chemistry 2011, 8(S1), S47-S52 Application of Green Chemistry Principle in Synthesis of Phenytoin and Its Biogical Evaluation as Anticonvulsant
More informationSynthesis and Antimicrobial Activity of Some New Isatin Derivatives
Iranian Journal of Pharmaceutical Research (2006) 4: 249-254 Received: August 2005 Accepted: July 2006 Copyright 2006 by School of Pharmacy Shaheed Beheshti University of Medical Sciences and Health Services
More informationSynthetic chemistry-led creation of a difluorinated biaryl ether non-nucleoside reverse transcriptase inhibitor
upplementary Material for rganic & Biomolecular Chemistry ynthetic chemistry-led creation of a difluorinated biaryl ether non-nucleoside reverse transcriptase inhibitor Lyn. Jones* Amy Randall, scar Barba
More informationEur. J. Org. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007 ISSN X SUPPORTING INFORMATION
Eur. J. Org. Chem. 2007 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 ISSN 1434 193X SUPPORTING INFORMATION Title: Effect of Varying the Anionic Component of a Copper(I) Catalyst on Homologation
More informationInternational Journal of Pharma and Bio Sciences V1(2)2010 SY THESES A D BIOLOGICAL ACTIVITY OF SOME 3, 5-DRIARYL-4H-1, 2, 4-TRIAZOLE DERIVATIVES
RAM JA AM SI GH *1 A D DHARME DRA KUMAR SI GH 2 1 Quality Control Laboratory, Indian Oil Corporation Limited, Panipat, Haryana-132140 (India) 1, 2 Synthetic Research Laboratory, Department of Chemistry,
More informationNitro-Grela-type complexes containing iodides. robust and selective catalysts for olefin metathesis
Supporting Information for Nitro-Grela-type complexes containing iodides robust and selective catalysts for olefin metathesis under challenging conditions. Andrzej Tracz, 1,2 Mateusz Matczak, 1 Katarzyna
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 6951 Weinheim, 2008 COMMUNICATION Copper or Iron Catalysed Arylation of Phenols from respectively Aryl Chlorides and Aryl Iodides Ning
More informationAn expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters
Indian Journal of Chemistry Vol. 53B, April 2014, pp. 392-398 An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters Padam
More informationph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors
ph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors Jie Li, Chendong Ji, Wantai Yang, Meizhen Yin* State Key Laboratory of Chemical Resource Engineering,
More informationSupporting Information Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C C Bond Cleavage of 2-Arylin
Supporting Information Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C C Bond Cleavage of 2-Arylindoles Wei-Li Chen, Si-Yi Wu, Xue-Ling Mo, Liu-Xu Wei,
More informationSolid Phase Peptide Synthesis (SPPS) and Solid Phase. Fragment Coupling (SPFC) Mediated by Isonitriles
Solid Phase Peptide Synthesis (SPPS) and Solid Phase Fragment Coupling (SPFC) Mediated by Isonitriles Ting Wang a and Samuel J. Danishefsky a,b,* alaboratory for Bioorganic Chemistry, Sloan- Kettering
More informationSupporting Information. Use of Potassium. -Trifluoroborato Amides in Suzuki-Miyaura. Cross-Coupling Reactions
Supporting Information Use of Potassium -Trifluoroborato Amides in Suzuki-Miyaura Cross-Coupling Reactions Gary A. Molander* and Ludivine Jean-Gérard Roy and Diana Vagelos Laboratories, Department of Chemistry,
More informationElectronic Supplementary Information
Electronic Supplementary Information A Novel and Facile Zn-mediated Intramolecular Five-membered Cyclization of β-tetraarylporphyrin Radicals from β-bromotetraarylporphyrins Dong-Mei Shen, Chao Liu, Qing-Yun
More informationSyntheses of aromatic aldehyde imine derivatives of 2-thiobenzyl-1,3,4-thiadiazole and evaluation of their anticonvulsant activity
Indian Journal of Chemistry Vol. 49B, February 2010, pp. 241-246 ote yntheses of aromatic aldehyde imine derivatives of 2-thiobenzyl-1,3,4-thiadiazole and evaluation of their anticonvulsant activity Bahar
More informationNaoya Takahashi, Keiya Hirota and Yoshitaka Saga* Supplementary material
Supplementary material Facile transformation of the five-membered exocyclic E-ring in 13 2 -demethoxycarbonyl chlorophyll derivatives by molecular oxygen with titanium oxide in the dark Naoya Takahashi,
More informationSYNTHESIS OF QUATERNARY AMMONIUM COMPOUNDS FROM NATURAL MATERIALS
Int. J. Chem. Sci.: 12(3), 2014, 880-884 ISSN 0972-768X www.sadgurupublications.com SYNTHESIS OF QUATERNARY AMMONIUM COMPOUNDS FROM NATURAL MATERIALS MUHAMMAD ABDUL QADIR, MAHMOOD AHMED *, SHOUKAT HAYAT,
More informationSIMAROUBA CEDRON FOR HOMOEOPATHIC PREPARATIONS CEDRON FOR HOMOEOPATHIC PREPARATIONS
SIMAROUBA CEDRON FOR HOMOEOPATHIC PREPARATIONS CEDRON FOR HOMOEOPATHIC PREPARATIONS Simaba cedron ad praeparationes homoeopathicas Other Latin name used in homoeopathy: Simaruba DEFINITION Dried cotyledons
More informationA Hierarchy of Aryloxide Deprotection by Boron Tribromide. Supporting Information
A Hierarchy of Aryloxide Deprotection by Boron Tribromide Sreenivas Punna, Stéphane Meunier and M. G. Finn* Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute,
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supporting Information Facile Three-Step Synthesis and Photophysical Properties of [8]-, [9]-,
More informationElectronic Supplementary Information. Quinine/Selectfluor Combination Induced Asymmetric Semipinacol Rearrangement of
Electronic Supplementary Information Quinine/Selectfluor Combination Induced Asymmetric Semipinacol Rearrangement of Allylic Alcohols: An Effective and Enantioselective Approach to α Quaternary β Fluoro
More informationCDI Mediated Monoacylation of Symmetrical Diamines and Selective Acylation of Primary Amines of Unsymmetrical Diamines
Supporting information: CDI Mediated Monoacylation of Symmetrical Diamines and Selective Acylation of Primary Amines of Unsymmetrical Diamines Sanjeev K. Verma*, Ramarao Ghorpade, Ajay Pratap and M. P.
More informationSupporting Information. An Efficient Synthesis of Optically Active Physostigmine from Tryptophan via Alkylative Cyclization
Supporting Information An Efficient Synthesis of Optically Active Physostigmine from Tryptophan via Alkylative Cyclization Michiaki, Kawahara, Atsushi Nishida, Masako Nakagawa* Faculty of Pharmaceutical
More informationCatalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water
SUPPORTING INFORMATION Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water Sunay V. Chankeshwara and Asit K. Chakraborti* National Institute of Pharmaceutical Education and Research
More informationSupporting information
Supporting information Diversity Oriented Asymmetric Catalysis (DOAC): Stereochemically Divergent Synthesis of Thiochromanes Using an Imidazoline-aminophenol aminophenol (IAP)-Ni Catalyzed Michael/Henry
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information ovel pseudo[2]rotaxanes constructed by selfassembly of dibenzyl
More informationAccessory Publication
10.1071/CH09088_AC CSIRO 2009 Accessory Publication: Australian Journal of Chemistry, 2009, 62(8), 790 793 Thermally Responsive Elastomeric Supramolecular Polymers Featuring Flexible Aliphatic Hydrogen
More informationβ-sitosterol-3-o-β-d-xylopyranosyl (1 4)-O-β-D- GLUCOPYRANOSIDE FROM THE SEEDS OF ZANTHOXYLUM HEMILTONIANUM WALL
Int. J. Chem. Sci.: 11(2), 201, 111-116 ISSN 0972-768X www.sadgurupublications.com β-sitsterl---β-d-xylpyransyl (1 4)--β-D- GLUCPYRANSIDE FRM TE SEEDS F ZANTXYLUM EMILTNIANUM WALL SANDYA RAJPT * Department
More informationSupporting Information
Palladium-Catalyzed Cascade Oxidantion/sp 2 C-H Acylation of Azoarenes with Aryl Methanes Feng Xiong, a Cheng Qian, b Dongen Lin, b Wei Zeng b,* and Xiaoxia Lu a,* a Chengdu Institute of Biology,CAS, Chengdu
More informationSynthesis and Analysis of N-Acetyltyrosine-N- Ethyl Amide from N-Acetyl Yyrosine Ethyl Ester
Governors State University OPUS Open Portal to University Scholarship All Capstone Projects Student Capstone Projects Fall 2010 Synthesis and Analysis of N-Acetyltyrosine-N- Ethyl Amide from N-Acetyl Yyrosine
More informationStudent Handout. This experiment allows you to explore the properties of chiral molecules. You have
Student Handout This experiment allows you to explore the properties of chiral molecules. You have learned that some compounds exist as enantiomers non-identical mirror images, such as your left and right
More informationSUPPORTING INFORMATION. Transition metal-promoted synthesis of 2-aryl/heteroaryl-thioquinazoline: C-S
1 SUPPORTING INFORMATION Transition metal-promoted synthesis of 2-aryl/heteroaryl-thioquinazoline: C-S Bond formation by Chan-Lam Cross-Coupling Reaction SATYA KARUNA PULAKHANDAM a, NARESH KUMAR KATARI
More informationRuthenium-Catalyzed C H Oxygenation on Aryl Weinreb Amides
Supporting Information Ruthenium-Catalyzed C H xygenation on Aryl Weinreb Amides Fanzhi Yang and Lutz Ackermann* Institut für rganische und Biomolekulare Chemie Georg-August-Universität Tammannstrasse
More informationSupporting Information. for. Synthesis of dye/fluorescent functionalized. dendrons based on cyclotriphosphazene
Supporting Information for Synthesis of dye/fluorescent functionalized dendrons based on cyclotriphosphazene Aurélien Hameau 1,2, Sabine Fuchs 1,2, Régis Laurent 1,2, Jean-Pierre Majoral* 1,2 and Anne-Marie
More informationHeparin Sodium ヘパリンナトリウム
Heparin Sodium ヘパリンナトリウム Add the following next to Description: Identification Dissolve 1 mg each of Heparin Sodium and Heparin Sodium Reference Standard for physicochemical test in 1 ml of water, and
More informationSupporting Information
Zinc-Mediated Addition of Diethyl Bromomalonate to Alkynes for the Cascade Reaction towards Polysubstituted Pyranones and Tetracarbonyl Derivatives Anne Miersch, Klaus Harms, and Gerhard Hilt* Fachbereich
More informationElectronic Supplementary Material
Electronic Supplementary Material PAMAM Dendrimers Bearing Electron-Donating Chromophores: Fluorescence and Electrochemical Properties Bing-BingWang a, Xin Zhang a, Ling Yang a, Xin-Ru Jia* a, Yan Ji a,
More informationIssue in Honor of Prof. Edmund Lukevics ARKIVOC 2006 (v) 86-91
Issue in onor of Prof. Edmund Lukevics ARKIVC 2006 (v) 86-91 Polycyclic heterocycles with acidic - groups VIII 1 The synthesis of some binuclear - acids with free rotary 1,2,4- triazole, 6-azauracil and
More informationElectronic Supplementary Information
Electronic Supplementary Information ~ Experimental Procedures and Spectral/Analytical Data ~ Use of Dimethyl Carbonate as a Solvent Greatly Enhances the Biaryl Coupling of Aryl Iodides and Organoboron
More informationPectins. Residue Monograph prepared by the meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA), 82 nd meeting 2016
Residue Monograph prepared by the meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA), 82 nd meeting 2016 Pectins This monograph was also published in: Compendium of Food Additive Specifications.
More informationA multicomponent CuAAC click approach. to a library of hybrid polydentate 2-pyridyl- the generation of metallosupramolecular. architectures.
Supporting information A multicomponent CuAAC click approach to a library of hybrid polydentate 2-pyridyl- 1,2,3-triazole ligands: New building blocks for the generation of metallosupramolecular architectures.
More informationSupporting Information. for. Synthesis of 2,1-benzisoxazole-3(1H)-ones by basemediated. photochemical N O bond-forming
Supporting Information for Synthesis of 2,1-benzisoxazole-3(1H)-ones by basemediated photochemical N O bond-forming cyclization of 2-azidobenzoic acids Daria Yu. Dzhons and Andrei V. Budruev* Address:
More informationSupporting Information File 1. for. Synthesis of functionalised β-keto amides by. aminoacylation/domino fragmentation of β-enamino amides
Supporting Information File 1 for Synthesis of functionalised β-keto amides by aminoacylation/domino fragmentation of β-enamino amides Pavel Yanev and Plamen Angelov* Address: Department of Organic Chemistry,
More informationSynthesis of Some 4-Thiazolidinone Derivatives as Antitubercular Agents
Journal of ciences, Islamic Republic of Iran 15(2): 143-148 (2004) University of Tehran, I 1016-1104 hort Communication ynthesis of ome 4-Thiazolidinone Derivatives as Antitubercular Agents H.H. Parekh,
More informationSupporting Information
Supporting Information Direct Synthesis of Benzimidazoles by Dehydrogenative Coupling of Aromatic Diamines and Alcohols Catalyzed by Cobalt Prosenjit Daw, Yehoshoa Ben-David, and David Milstein* Department
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 Supporting Information General. NMR spectra for identification of intermediates and final compoundswere recorded
More informationFacile Cu(II) mediated conjugation of thioesters and thioacids to peptides and proteins under mild conditions
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Facile Cu(II) mediated conjugation of thioesters and thioacids to peptides
More informationSupporting Information for
Supporting Information for Tandem Mass Spectrometry Assays of Palmitoyl Protein Thioesterase and Tripeptidyl Peptidase Activity in Dried Blood Spots for the Detection of Neuronal Ceroid Lipofuscinoses
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Enantioselective Rhodium-catalyzed Addition of Arylboronic Acids to α-ketoesters Hai-Feng Duan, Jian-Hua Xie, Xiang-Chen Qiao, Li-Xin Wang,
More informationDesign, synthesis and evaluation of ph-dependent hydrolysable emetine analogs as treatment for prostate cancer.
Design, synthesis and evaluation of p-dependent hydrolysable emetine analogs as treatment for prostate cancer. Emmanuel S. Akinboye, 1 Marc D. Rosen, 2 Samuel R. Denmeade, 2 Bernard Kwabi-Addo 3 and ladapo
More informationEfficient Metal-Free Pathway to Vinyl Thioesters with Calcium Carbide as the Acetylene Source
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Efficient Metal-Free Pathway to Vinyl Thioesters with Calcium Carbide
More informationEnzymatic resolution and evaluation of enantiomers of. cis-5 -hydroxythalidomide
Electronic Supplementary Information Enzymatic resolution and evaluation of enantiomers of cis-5 -hydroxythalidomide Takeshi Yamamoto, a orio Shibata, a * Masayuki Takashima, a Shuichi akamura, a Takeshi
More information