SUPPORTING INFORMATION. Transition metal-promoted synthesis of 2-aryl/heteroaryl-thioquinazoline: C-S

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1 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 *,b and RAVI PRAKASH REDDY MANDA c a Jawaharlal Nehru Technological University Kakinada, Kakinada , Andhra Pradesh, India karunasathya@gmail.com * b Department of Chemistry, GITAM School of Technology, GITAM University, HTP Campus, Rudraram, Medak , Telangana, India dr.n.k.katari@gmail.com c C-MET, IDA Phase II, Cherlapally, HCL (PO), Hyderabad , Telangana, India mrpreddy@yahoo.com General Information Reagents and solvents obtained from commercial suppliers were used without purification or drying unless otherwise noted. The compounds are synthesized and characterization, conformation with different analytical techniques under the following instruments. i) 1 HNMR: 1 H NMR were recorded using Agilent instrument at 300 MHz, Bruker instrument at 400 MHz, using CDCl3, DMSO-d6 as solvents and Trimethyl silane (TMS) was used as an internal standard.

2 2 ii) 13 CNMR: 13 C NMR were recorded using Agilent instrument at 300 MHz, Bruker instrument at 400 MHz and using CDCl3, DMSO-d6 as solvents and Trimethyl silane (TMS) was used as an internal standard. iii) LC-MS: LCMS analysis was performed on water UPLC with SQD-2 mass detector (Single quadrapole). Under the following conditions. Condition-A: Column: AQUITY UPLC BEH C18, 1.7 µm, 2.1 x 50 mm, Mobile phase A: 0.1% FA in ACN, Mobile phase B: 0.1% FA in H2O, T% of B: 0/97, 0.3/97, 3.2/2, 4/2, 4.01/97.; Flow-0.6 ml/min, Temp: 35 o C. Condition-B: Column: AQUITY UPLC BEH C18 (2.1 x 50 mm, 1.7 µm), Mobile phase A1: 0.1% FA in Water, Mobile phase B: 0.1% FA in ACN, Gradient: Time (min)/% of B: 0/3, 0.2/3, 2.8/98, 4.0/98, 4.5/3.; Flow-0.6 ml/min, Temp: 35 o C. iv) IR: Fourier-transform spectrometer was given absorption spectra for solid, liquid compounds. v) MR: BUCHI Corporation M-565 instrument for identify melting range of solid compounds. vi) Hazardous: All products are smelly compounds. General experimental procedure: Compounds a to r were prepared by following a general synthetic procedure in which the solution of 1,4-dihydroquinazoline-2-thiol (100 mg, mmol) in dichloromethane (4 ml) were added the Cu(OAc)2 (166 mg, mmol), Et3N (0.43 ml, mmol) and stirred for min at RT, followed by addition of substituted boronic acid (1.219 mmol) and the reaction mixture was stirred at RT for 12 h. After completion of the reaction, as indicated by TLC, the reaction mixture was quenched with water (10 ml) and extracted

3 3 with dichloromethane (2 x15 ml). The organic layer was washed with water, brine solution and dried over anhydrous Na2SO4, filtered the solvent, concentrated under reduced pressure to give crude compound. The crude compound was purified by flash column chromatography ( mesh silica gel), eluted at % ethyl acetate/pet ether to afford the S-substituted quinazoline derivative. The physical data (Nature, quantity, yield, Rf value and column elution percentage) and spectral data ( 1 HNMR, 13 CNMR, LC-MS, MR and IR) of these synthesized compounds are reported below. Table S4. Substituent effects in the cross coupling of thiol with substituted boronic acid. Entry Boronic acid (2) Product b (3) Yield a (%) a N N S 85 b HO B N N S 77 OH HO B OH c N N S 87

4 4 d HO B OH N N N N S 86 e HO OH B O N N S O 90 f OH B OH N NO 2 88 NO 2 N S

5 5 g HO OH B S CHO N N S S CHO 92 h S OH B OH N N S S 82 Cl i Cl HO B OH N N S Cl Cl 87 j N OH B OH N N S N 83

6 6 k OH B OH N N S 90 l HO OH B Br N N S Br 82 OCF 3 m B HO OH N N S OCF 3 76 n HO OH B O N N S O 72

7 7 HO B OH CF 3 80 o N CF 3 N S OH B OH N N S 90 p N q B OH OH N S 85 O O r HO B OH N O N N S N O 90 a Isolated yields. b All the compounds were characterized by IR, 1 H NMR, 13 C NMR spectroscopy and mass spectrometry.

8 8 LIST OF FIGURES Fig. No. Figure Name Page No. 2.2a 1 H NMR spectrum of 2-(p-tolylthio)quinazoline (1) a Mass spectrum of 2-(p-tolylthio)quinazoline (1) a 13 CNMR spectrum of 2-(p-tolylthio)quinazoline (1) a IR spectrum of 2-(p-tolylthio)quinazoline (1) a MR spectrum of 2-(p-tolylthio)quinazoline (1) b 1 H NMR spectrum of 2-Allylsulfanyl-quinazoline (2) b Mass spectrum of 2-Allylsulfanyl-quinazoline (2) b 13 CNMR spectrum of 2-Allylsulfanyl-quinazoline (2) b IR spectrum of 2-Allylsulfanyl-quinazoline (2) c 1 H NMR spectrum of (4-Isopropyl-phenylsulfanyl)-quinazoline (3) 2.2c Mass spectrum of (4-Isopropyl-phenylsulfanyl)-quinazoline (3) 2.2c 13 CNMR spectrum of 2-(p-tolylthio)quinazoline (3) c IR spectrum of 2-(4-Isopropyl-phenylsulfanyl)-quinazoline 23 (3) 2.2d 1 H NMR spectrum of 2-(pyridin-4-ylsulfanyl)-quinazoline 24 (4) 2.2d Mass spectrum of 2-(pyridin-4-ylsulfanyl)-quinazoline (4) d 13 CNMR spectrum of 2-(p-tolylthio)quinazoline (4) d IR spectrum of 2-(pyridin-4-ylsulfanyl)-quinazoline (4) d MR spectrum of 2-(pyridin-4-ylsulfanyl)-quinazoline (4) e 1 H NMR spectrum of 28 2-(3-Methoxy-phenylsulfanyl)-quinazoline (5) 2.2e Mass spectrum of (3-Methoxy-phenylsulfanyl)-quinazoline (5) 2.2e 13 CNMR spectrum of 2-(3-Methoxy-phenylsulfanyl)-quinazoline (5) 2.2e IR spectrum of 2-(3-Methoxy-phenylsulfanyl)-quinazoline (5) 2.2e MR spectrum of 2-(3-Methoxy-phenylsulfanyl)-quinazoline (5)

9 9 2.2f 1 H NMR spectrum of 33 2-(3-Nitro-phenylsulfanyl)-quinazoline (6) 2.2f 13 CNMR spectrum of 34 2-(3-Nitro-phenylsulfanyl)-quinazoline (6) 2.2f Mass spectrum of 2-(3-Nitro-phenylsulfanyl)-quinazoline (6) 2.2f IR spectrum of 2-(3-Nitro-phenylsulfanyl)-quinazoline (6) f MR spectrum of 2-(3-Nitro-phenylsulfanyl)-quinazoline 38 (6) 2.2g 1 H NMR spectrum of 39 5-(quinazolin-2-ylthio)thiophen-2-carbaldehyde (7) 2.2g Mass spectrum of (quinazolin-2-ylthio)thiophen-2-carbaldehyde (7) 2.2g IR spectrum of 42 5-(quinazolin-2-ylthio)thiophen-2-carbaldehyde (7) 2.2g MR spectrum of 43 5-(quinazolin-2-ylthio)thiophen-2-carbaldehyde (7) 2.2h 1 H NMR spectrum of 44 2-(benzo[b]thiophen-2-ylthio)quinazoline (8) 2.2h Mass spectrum of 45 2-(benzo[b]thiophen-2-ylthio)quinazoline (8) 2.2h 13 CNMR spectrum of 46 2-(benzo[b]thiophen-2-ylthio)quinazoline (8) 2.2h IR spectrum of 2-(benzo[b]thiophen-2-ylthio)quinazoline (8) h MR spectrum of 47 2-(benzo[b]thiophen-2-ylthio)quinazoline (8) 2.2i 1 H NMR spectrum of 48 2-((2,3-dichlorophenyl)thio)quinazoline (1) 2.2i Mass spectrum of 2-((2,3-dichlorophenyl)thio)quinazoline (9) i 13 CNMR spectrum of 51 2-((2,3-dichlorophenyl)thio)quinazoline (9) 2.2i IR spectrum of 2-((2,3-dichlorophenyl)thio)quinazoline (9) i MR spectrum of 2-(p-tolylthio)quinazoline (9) 52

10 10 2.2j 1 H NMR spectrum of 53 2-(Quinolin-3-ylsulfanyl)-quinazoline (10) 2.2j Mass spectrum of 2-(Quinolin-3-ylsulfanyl)-quinazoline (10) j 13 CNMR spectrum of 55 2-(Quinolin-3-ylsulfanyl)-quinazoline (10) 2.2j IR spectrum of 2-(Quinolin-3-ylsulfanyl)-quinazoline (10) j MR spectrum of 2-(Quinolin-3-ylsulfanyl)-quinazoline 56 (10) 2.2k 1 H NMR spectrum of 2-Phenethylsulfanyl-quinazoline (11) k Mass spectrum of 2-Phenethylsulfanyl-quinazoline (11) k 13 CNMR spectrum of 2-Phenethylsulfanyl-quinazoline (11) k IR spectrum of 2-Phenethylsulfanyl-quinazoline (11) l 1 H NMR spectrum of 2-((3-bromophenyl)thio) quinazoline 60 (12) 2.2l Mass spectrum of 2-((3-bromophenyl)thio) quinazoline 61 (12) 2.2l 13 CNMR spectrum of 2-((3-bromophenyl)thio) quinazoline 62 (12) 2.2l IR spectrum of 2-((3-bromophenyl)thio) quinazoline (12) m 1 H NMR spectrum of 63 2-(4-Trifluoromethoxy-phenylsulfanyl)-quinazoline (13) 2.2m Mass spectrum of 2-(p-tolylthio)quinazoline (13) m 13 CNMR spectrum of 2-(p-tolylthio)quinazoline (13) m IR spectrum of 2-(p-tolylthio)quinazoline (13) n 1 H NMR spectrum of 2-(Furan-2-ylsulfanyl)-quinazoline 67 (14) 2.2n Mass spectrum of 2-(Furan-2-ylsulfanyl)-quinazoline (14) n 13 CNMR spectrum of 2-(Furan-2-ylsulfanyl)-quinazoline 69 (14) 2.2n IR spectrum of 2-(Furan-2-ylsulfanyl)-quinazoline (14) o 1 H NMR spectrum of 70 2-((3-(trifluoromethyl)phenyl)thio)quinazoline (15) 2.2o Mass spectrum of ((3-(trifluoromethyl)phenyl)thio)quinazoline (15)

11 11 2.2o 13 CNMR spectrum of 73 2-((3-(trifluoromethyl)phenyl)thio)quinazoline (15) 2.2o IR spectrum of 73 2-((3-(trifluoromethyl)phenyl)thio)quinazoline (15) 2.2p 1 H NMR spectrum of 2-(naphthalen-2-ylthio)quinazoline 74 (16) 2.2p Mass spectrum of 2-(naphthalen-2-ylthio)quinazoline (16) p 13 CNMR spectrum of 2-(naphthalen-2-ylthio)quinazoline 77 (16) 2.2p IR spectrum of 2-(naphthalen-2-ylthio)quinazoline (16) q 1 H NMR spectrum of 2-(biphenyl-2-ylthio)quinazoline (17) q Mass spectrum of 2-(biphenyl-2-ylthio)quinazoline (17) q 13 CNMR spectrum of 2-(biphenyl-2-ylthio)quinazoline (17) q IR spectrum of 2-(biphenyl-2-ylthio)quinazoline (17) r 1 H NMR spectrum of 82 Morpholine(4-(quinazolin-2-ylthio)phenyl)methanone (18) 2.2r Mass spectrum of 83 Morpholine(4-(quinazolin-2-ylthio)phenyl)methanone (18) 2.2r 13 CNMR spectrum of 84 Morpholine(4-(quinazolin-2-ylthio)phenyl)methanone (18) 2.2r IR spectrum of 84 Morpholine(4-(quinazolin-2-ylthio)phenyl)methanone (18)

12 12 List of the Analytical & Spectral Data 2.2a 2-(p-tolylthio) quinazoline (table 4, Entry a): Pale yellow solid. [Yield: 130 mg, 85 %] Rf : 0.7, 8 % EtOAc/Pet ether; Analysis: LC-MS: m/z C15H12N2S for (M+H): Calculated: 252.3; Found, (82.3 %). IR / cm -1 : , , , , , , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.15 (1H, s), (3H, m), (3H, m), 7.35 (1H, t, J = 7.6 Hz), 7.25 (1H, d, J = 2.0 Hz), 2.40 (3H, s). 13 C NMR (CDCl3, 300 MHz): , , , , , , , , , , , , 105.0, ppm. MR: o C.

13 13

14 14

15 15

16 16

17 17 2.2b 2-Allylsulfanyl-quinazoline (table 4, Entry b): Yellow thick mass. [Yield: 95 mg, 77 %] Rf : 0.6, 8 % EtOAc/Pet ether; Analysis: LC-MS: m/z C11H10N2S for (M+H): Calculated: ; Found, (99.64 %). IR / cm -1 : , , , , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.14 (1H, s), (3H, m), (1H, m), (1H, m), 5.38 (1H, dd, J = 17.2, 1.0 Hz), 5.15 (1H, d, J = 9.6 Hz), 3.96 (2H, d, J = 7.2 Hz). 13 C NMR (CDCl3, 400 MHz): , , , , , , , , , , ppm.

18 18

19 19

20 20 2.2c 2-(4-Isopropyl-phenylsulfanyl)-quinazoline (table 4, Entry c): Pale Yellow thick mass [Yield: 147 mg, 87%] Rf : 0.7, 10 % EtOAc/Pet ether; Analysis: LC-MS: m/z C17H16N2S for (M+H): Calculated: ; Found, (83 %). IR / cm -1 : , , , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.16 (1H, s), (3H, m), 7.51 (2H, t, J = 7.4 Hz), (2H, m), 7.30 (1H, d, J = 8.0 Hz), (1H, m), 1.56 (6H, d, J = 8.0 Hz). 13 C NMR (CDCl3, 300 MHz): , , , , , , , , , , , , 34.67, 29.88, ppm.

21 21

22 22

23 23

24 24 2.2d 2-(pyridin-4-ylsulfanyl)-quinazoline (table 4, Entry d): Off white solid [Yield: 125 mg, 86%] Rf : 0.2, 20 % EtOAc/Pet ether; Analysis: LC-MS: m/z C13H9N3S for (M+H): Calculated: ; Found, (94.51 %); IR / cm -1 : , , , , , , , , , , , , and H-NMR (CDCl3, 400 MHz): 9.16 (1H, s), 8.8 (2H, s), 8.04 (1H, d, J = 8.0 Hz), 7.83 (2H, t, J = 7.6 Hz), 7.75 (1H, d, J = 8.4 Hz), 7.54 (1H, t, J = 7.80 Hz), 7.45 (1H, s). 13 C NMR (CDCl3, 400 MHz): , , , , , , , ppm. MR: o C.

25 25

26 26

27 27

28 28 2.2e 2-(3-Methoxy-phenylsulfanyl)-quinazoline (table 4, Entry e): Pale yellow solid [Yield: 146 mg, 90%] Rf : 0.7, 10 % EtOAc/Pet ether; Analysis: LC-MS: m/z C15H12N2OS for (M+H): Calculated: ; Found, (98.49 %); IR / cm -1 : , , , , , , , , , , , , and H-NMR (DMSO-d6, 300 MHz): 9.36 (1H, s), 8.04 (1H, d, J = 8.10 Hz), 7.92 (1H, t, J = 7.05 Hz), (3H, m), (1H, m), 7.17 (1H, d, J = 8.40 Hz), 7.05 (1H, t, J = 7.50 Hz), 3.7 (3H, s). 13 C NMR (CDCl3, 400 MHz): , , , , , , , , , , , , , , ppm. MR: o C.

29 29

30 30

31 31

32 32

33 33 2.2f 2-(3-Nitro-phenylsulfanyl)-quinazoline (table 4, Entry f) Yellow solid [Yield: 152 mg, 88%] Rf : 0.6, 12 % EtOAc/Pet ether; Analysis: LC-MS: m/z C14H9N3O2S for (M+H): Calculated: ; Found, (96.58 %); IR / cm -1 : , , , , , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.20 (1H, s), 8.28 (2H, d, J = 3.60 Hz), (4H, m), 7.80 (1H, d, J = 8.80 Hz), (1H, m). 13 C NMR (CDCl3, 300 MHz): 160.8, , , , , , , , , 127.5, , , MR: o C.

34 34

35 35

36 36

37 37

38 38

39 39 2.2g 5-(quinazolin-2-ylthio)thiophen-2-carbaldehyde (table 4, Entry g): Pale yellow solid [Yield: 152 mg, 92%] Rf : 0.5, 15 % EtOAc/Pet ether; Analysis: LC-MS: m/z C13H8N2OS2 for (M+H): Calculated: ; Found, (92.29 %); IR / cm -1 : , , , , , , , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.92 (1H, s), 9.22 (1H, s), (3H, m), 7.76 (1H, d, J = 3.0 Hz), (1H, m), 7.43 (1H, t, J = 2.85 Hz). MR: o C.

40 40

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42 42

43 43

44 44 2.2h 2-(benzo[b]thiophen-2-ylthio)quinazoline (table 4, Entry h): Yellow solid [Yield: 147 mg, 82%] Rf : 0.4, 17 % EtOAc/Pet ether; Analysis: LC-MS: m/z C16H10N2S2 for (M+H): Calculated: ; Found, (85.65 %); IR / cm -1 : , , , , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.19 (1H, s), (6H, m), 7.66 (1H, s), (1H, m), (1H, m). 13 C NMR (CDCl3, 400 MHz): , , , , , , , , , , , , , ppm. MR: o C.

45 45

46 46

47 47

48 48 2.2i 2-((2,3-dichlorophenyl)thio)quinazoline (table 4, Entry i): Off white solid [Yield: 162 mg, 87%] Rf : 0.7, 10 % EtOAc/Pet ether; Analysis: LC-MS: m/z C14H8Cl2N2S for (M+H, M+3H): Calculated: ; Found, 307.0, (92.36 %); IR / cm -1 : , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.17 (1H, s), (4H, m), (3H, m). 13 C NMR (CDCl3, 400 MHz): , , , , , , , , , , , , , ppm. MR: o C.

49 49

50 50

51 51

52 52

53 53 2.2j 2-(Quinolin-3-ylsulfanyl)-quinazoline (table 4, Entry j): Off white solid [Yield: 146 mg, 83%] Rf : 0.2, 10 % EtOAc/Pet ether; Analysis: LC-MS: m/z C17H11N3S for (M+H): Calculated: ; Found, (98.58 %); IR / cm -1 : , , , , , , , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.11 (1H, s), 8.98 (1H, dd, J = 4.4, 1.6 Hz), (3H, m), 7.98 (1H, dd, J = 8.8, 6.4 Hz), (3H, m), (1H, m), (1H, m). 13 C NMR (CDCl3, 300 MHz): 160.9, , , , , , , , , 129.0, , , , 127.0, , ppm. MR: o C.

54 54

55 55

56 56

57 57 2.2k 2-Phenethylsulfanyl-quinazoline (table 4, Entry k): Yellow thickmass [Yield: 146 mg, 90%] Rf : 0.7, 8 % EtOAc/Pet ether; Analysis: LC-MS: m/z C16H14N2S for (M+H): Calculated: ; Found, (98.96 %). IR / cm -1 : , , , , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.16 (1H, s), (3H, m), (1H, m), (4H, m), (1H, m), 3.51 (2H, t, J = 9.6 Hz), 3.13 (2H, t, J = 7.6 Hz). 1 HNMR (DMSO-d6, 400 MHz): , , , , , , , , , , , , 48.57, ppm.

58 58

59 59

60 60 2.2l 2-((3-bromophenyl)thio) quinazoline (table 4, Entry l): Yellow thick mass [Yield: 158 mg, 82%] Rf : 0.8, 5 % EtOAc/Pet ether; Analysis: LC-MS: m/z C14H9BrN2S for (M+H, M+3H): Calculated: ; Found, , (97.34 %). IR / cm -1 : , , , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.15 (1H, s), (4H, m), (2H, m), (1H, m), (1H, m). 13 C NMR (CDCl3, 300 MHz): , 151.0, , , , , , , , , , , ppm.

61 61

62 62

63 63 2.2m 2-(4-Trifluoromethoxy-phenylsulfanyl)-quinazoline (table 4, Entry m): Yellow oil [Yield: 149 mg, 76%] Rf : 0.5, 15 % EtOAc/Pet ether; Analysis: LC-MS: m/z C15H9F3N2OS for (M+H): Calculated: ; Found, (90.42 %). IR / cm -1 : , , , , , , , , and HNMR (CDCl3, 300 MHz): 9.18 (1H, s), (2H, m), 7.76 (1H, d, J = 8.4 Hz), 7.64 (2H, t, J = 12.4 Hz), (1H, m), 7.47 (1H, t, J = 8.1 Hz), 7.30 (1H, s). 13 C NMR (CDCl3, 300 MHz): , , 158.4, , , , , 130.0, 129.1, , 125.6, 122.2, 121.7, 115.0, ppm.

64 64

65 65

66 66

67 67 2.2n 2-(Furan-2-ylsulfanyl)-quinazoline (table 4, Entry n): Yellow thick mass [Yield: 100 mg, 72%] Rf : 0.5, 15 % EtOAc/Pet ether; Analysis: LC-MS: m/z C12H8N2OS for (M+H): Calculated: ; Found, (90.13 %). IR / cm -1 : , , , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.16 (1H, s), 8.22 (1H, s), (2H, m), (2H, m), (2H, m). 13 C NMR (CDCl3, 300 MHz): , , , , , , , , , , , ppm.

68 68

69 69

70 70 2.2o 2-((3-(trifluoromethyl)phenyl)thio)quinazoline (table 4, Entry o): Yellow thick mass [Yield: 149 mg, 80%] Rf : 0.6, 12 % EtOAc/Pet ether; Analysis: LC-MS: m/z C15H9F3N2S for (M+H): Calculated: ; Found, (92.60 %). IR / (cm -1 ): , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.17 (1H, s), 8.01 (1H, s), 7.76 (1H, d, J = 8.8 Hz), 7.69 (1H, d, J = 8.0 Hz), (2H, m), 7.35 (1H, t, J = 8.0 Hz), 7.76 (1H, d, J = 7.6 Hz), 7.00 (1H, d, J = 8.4 Hz). 13 C NMR (CDCl3, 300 MHz): 160.7, 155.2, 150.6, 134.7, 132.6, 132.7, 131.8, 129.4, 129.3, 128.4, 127.6, 126.5, 125.7, 122.7, ppm.

71 71

72 72

73 73

74 74 2.2p 2-(naphthalen-2-ylthio) quinazoline (table 4, Entry p): Colorless oil [Yield: 158 mg, 90%] Rf : 0.6, 10 % EtOAc/Pet ether; Analysis: LC-MS: m/z C18H12N2S for (M+H): Calculated: ; Found, (93.94 %). IR / cm -1 : , , , , , , , , , , , , and HNMR (CDCl3, 300 MHz): 9.17 (1H, s), (3H, m), 7.77 (1H, s), 7.58 (1H, d, J = 1.2 Hz), (2H, m), (2H, m), 6.67 (1H, s). 13 C NMR (CDCl3, 300 MHz): , 151.0, , , 134.6, 128.4, 127.6, 127.3, 127.2, 126.6, 122.6, , 111.4, ppm.

75 75

76 76

77 77

78 78 2.2q 2-(biphenyl-2-ylthio) quinazoline (table 4, Entry q): Yellow thick mass [163 mg, Y: 85%] Rf : 0.7, 12 % EtOAc/Pet ether; Analysis: LC-MS: m/z C20H14N2S for (M+H): Calculated: ; Found, (85.68 %). IR / cm -1 : , , , , , , , , , and HNMR (CDCl3, 400 MHz): 9.17 (1H, s), 7.95 (1H, s), (2H, m), (3H, m), (2H, m), (2H, m), (1H, m), (1H, m), 6.77 (1H, s). 13 C NMR (CDCl3, 400 MHz): , , , , , 134.9, 128.6, , 127.5, 127.3, 125.7, 123.2, 123.0, 121.6, 117, ppm.

79 79

80 80

81 81

82 82 2.2r Morpholine(4-(quinazolin-2-ylthio)phenyl)methanone (table 4, Entry r): Pale yellow oil [Yield: 192 mg, 90%] Rf : 0.6, 12% EtOAc/Pet ether; Analysis: LC-MS: m/z C19H17N3O2S for (M+H): Calculated: ; Found, (92.77 %). IR / cm -1 : , , , , , , , , , , , , , and HNMR (CDCl3, 300 MHz): 9.15 (1H, s), (2H, m), (3H, m), (3H, m), (8H, m). 13 C NMR (CDCl3, 300 MHz): , , , , , , , , , , , , , 66.68, ppm.

83 83

84 84

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