Supporting Information
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1 Supporting Information A Regioselective Ring-Expansion of Isatins with In-situ Generated α-aryldiazomethanes; Direct Access to Viridicatin Alkaloids Yellaiah Tangella,, Kesari Lakshmi Manasa,, Namballa Hari Krishna,, B. Sridhar, Ahmed Kamal*,, and Bathini Nagendra Babu*,,, Fluoro-Agrochemicals, Centre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad , India Academy of Scientific and Innovative Research (AcSIR), New Delhi , India Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad , India. School of Pharmaceutical Education and Research (SPER), Jamia Hamdard University, New Delhi , India bathini@iict.res.in Contents General information..s2 X-ray crystal structure and crystal data of 4j S2 References..S3 General procedure for the synthesis of 4 and 5.S4 Characterization data for compounds 4 and 5..S4 Procedure and characterization data for the synthesis of 6, 7 and 8 S19 Copies of 1 H NMR and 13 C NMR spectra of 4, 5, 6, 7 and 8..S21 1
2 General Information All solvents and reagents were purchased from commercial suppliers and used without any further purification. The methyl- and benzyl- protected isatins were prepared according to the literature. All the reagents were handled and weighed in the air at room temperature. Thin layer chromatography (TLC) was performed using pre-coated silica gel 60 F254 MERCK. TLC plates were visualized by exposure to UV light. Silica gel (60 120) column chromatography was performed by using indicated solvent system. 1 H and 13 C NMR spectra were recorded relative to tertramethylsilane (TMS) and chemical shifts were reported in parts per million (δ). Melting points were recorded on an Electrothermal melting apparatus and are uncorrected. HRMS were performed on an ESI-QTOF mass spectrometer. X-ray Crystallography: 3-Hydroxy-4-(4-methoxyphenyl)-1-methylquinolin-2(1H)-one (4j) (CCDC: ) O OH N O Figure S1. X-Ray crystal structure of 4j, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented by circles of arbitrary radii. 2
3 X-ray data for the compound 4j was collected at room temperature on a Bruker D8 QUEST instrument with an IµS Mo microsource (λ = A) and a PHOTON-100 detector. The raw data frames were reduced and corrected for absorption effects using the Bruker Apex 3 software suite programs. 1 The structure was solved using intrinsic phasing method 2 and further refined with the SHELXL 2 program and expanded using Fourier techniques. Anisotropic displacement parameters were included for all non-hydrogen atoms. O bound H atom was located in difference Fourier maps and their positions and isotropic displacement parameters were refined. All other C bound H atoms were positioned geometrically and treated as riding on their parent C atoms [C-H = Å, and U iso (H) = 1.5U eq (C) for methyl H or 1.2U eq (C) for other H atoms]. Crystal Data for KA244: C 17 H 15 NO 3 (M = g/mol): monoclinic, space group P2 1 /n (no. 14), a = (1) Å, b = (5) Å, c = (2) Å, β = (7), V = (5) Å 3, Z = 4, T = K, µ(mo Kα) = mm -1, Dcalc = g/cm 3, reflections measured (5.34 2Θ ), 4330 unique (R int = , R sigma = ) which were used in all calculations. The final R 1 was (I>2σ(I)) and wr 2 was (all data). CCDC contains supplementary Crystallographic data for the structure. These data can be obtained free of charge at [or from the Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0) ; deposit@ccdc.cam.ac.uk]. References: 1. Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. 2. Sheldrick, G. M. Acta Cryst. 2015, C71,
4 General procedure for the synthesis of 4 and 5: A mixture of aldehydes (2, 1 mmol) and p- toluenesulfonyl hydrazide (3, 1 mmol) in ethanol was stirred at room temperature until complete consumption of starting materials (monitored by TLC). Then, isatins (1, 1 mmol) and K 2 CO 3 (2 mmol) was added to the reaction mixture and stirred at 80 o C for 8 h. After the reaction was finished, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (Petroleum ether/ethyl acetate) to afford the desired products 4 and 5. 3-Hydroxy-4-phenylquinolin-2(1H)-one (4a or II): By following the general procedure, 4a was purified by silica gel chromatography (EA/PE = 20/80). White solid; Yield: 203 mg (86%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.16 (s, 1H), 7.45 (t, J = 7.2 Hz, 2H), 7.37 (t, J = 7.3 Hz, 1H), 7.28 (t, m, 4H), (m, 2H); 13 C NMR (101 MHz, DMSO d 6 ) δ 158.7, 142.9, 134.2, 133.6, 130.3, 128.8, 128.1, 126.9, 124.7, 124.4, 122.6, 121.4, 115.7; MS (ESI): m/z 238 [M + H] + ; HRMS (ESI): m/z calcd for C 15 H 12 O 2 N: ; found: [M + H] +. 3-Hydroxy-4-(4-methoxyphenyl)quinolin-2(1H)-one (4b): By following the general procedure, 4b was purified by silica gel chromatography (EA/PE = 30/70). White solid; Yield: 248 mg (93%); mp: o C; 1 H NMR (400 MHz, DMSO d 6 ) δ (s, 1H), 9.11 (s, 1H), 7.31 (dt, J = 16.3, 7.4 Hz, 4H), 7.10 (dt, J = 13.3, 8.2 Hz, 4H), 3.83 (s, 3H); 13 C NMR (101 MHz, DMSO d 6 ) δ 159.1, 158.7, 142.9, 133.6, 131.6, 126.8, 126.0, 124.9, 124.2, 122.5, 121.6, 115.7, 114.2, 55.6; MS (ESI): m/z 268 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 14 O 3 N: ; found: [M + H] +. 4
5 3-Hydroxy-4-(3-methoxyphenyl)quinolin-2(1H)-one (4c): By following the general procedure, 4c was purified by silica gel chromatography (EA/PE = 30/70). Off white solid; Yield: 245 mg (92%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.21 (s, 1H), 7.43 (t, J = 7.9 Hz, 1H), 7.33 (bs, 2H), 7.07 (s, 2H), 7.01 (d, J = 7.4 Hz, 1H), 6.88 (d, J = 7.2 Hz, 2H), 3.78 (s, 3H); 13 C NMR (101 MHz, DMSO d 6 ) δ 159.7, 158.7, 142.8, 135.6, 133.6, 129.9, 126.9, 124.8, 124.3, 122.6, 122.5, 121.3, 115.9, 115.7, 113.6, 55.5; MS (ESI): m/z 268 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 14 O 3 N: ; found: [M + H] +. 3-Hydroxy-4-(2-methoxyphenyl)quinolin-2(1H)-one (4d): By following the general procedure, 4d was purified by silica gel chromatography (EA/PE = 35/65). White solid; Yield: 235 mg (88%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.09 (s, 1H), (m, 1H), 7.29 (q, J = 7.9 Hz, 2H), (m, 2H), (m, 2H), 6.83 (d, J = 7.9 Hz, 1H), 3.65 (s, 3H); 13 C NMR (75 MHz, DMSO d 6 ) δ 158.3, 156.6, 142.8, 132.9, 131.0, 129.4, 126.1, 124.3, 122.3, , 121.4, 121.0, 120.4, 115.0, 111.4, 55.2; MS (ESI): m/z 268 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 14 O 3 N: ; found: [M + H] +. 4-(4-Chlorophenyl)-3-hydroxyquinolin-2(1H)-one (4e): 5
6 By following the general procedure, 4e was purified by silica gel chromatography (EA/PE = 25/75). Off white solid; Yield: 227 mg (84%); mp: o C; 1 H NMR (400 MHz, DMSO d 6 ) δ (s, 1H), 9.20 (s, 1H), 7.52 (dd, J = 10.1, 4.5 Hz, 2H), (m, 1H), (m, 3H), (m, 2H); 13 C NMR (75 MHz, DMSO d 6 ) δ 158.1, 142.6, 133.1, 132.5, 132.4, 131.8, 128.4, 126.5, 124.0, 122.6, 122.2, 120.5, 115.3; MS (ESI): m/z 272 [M + H] + ; HRMS (ESI): m/z calcd for C 15 H 11 O 2 NCl: ; found: [M + H] +. 3-Hydroxy-4-(4-nitrophenyl)quinolin-2(1H)-one (4f): By following the general procedure, 4f was purified by silica gel chromatography (EA/PE = 35/65). Pale yellow solid; Yield: 223 mg (79%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.67 (s, 1H), 8.37 (d, J = 8.7 Hz, 2H), 7.66 (d, J = 8.7 Hz, 2H), (m, 2H), 7.10 (ddd, J = 8.1, 5.3, 2.9 Hz, 1H), 7.01 (d, J = 8.0 Hz, 1H); 13 C NMR (101 MHz, DMSO d 6 ) δ 158.4, 147.4, 143.3, 141.5, 133.6, 132.0, 127.2, 124.3, 124.0, 122.8, 122.4, 120.4, 115.9; MS (ESI): m/z 283 [M + H] + ; HRMS (ESI): m/z calcd for C 15 H 11 O 4 N 2 : ; found: [M + H] +. 4-(2-Ethoxyphenyl)-3-hydroxyquinolin-2(1H)-one (4g): By following the general procedure, 4gwas purified by silica gel chromatography (EA/PE = 30/70). Off white solid; Yield: 239 mg (85%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.06 (s, 1H), (m, 1H), 7.30 (d, J = 6.3 Hz, 2H), (m, 2H), 7.04 (td, J = 7.8, 4.0 Hz, 2H), 6.88 (d, J = 8.0 Hz, 1H), 3.98 (qd, J = 6.9, 2.4 Hz, 2H), 1.04 (t, J = 6.9 Hz, 3H); 13 C NMR (75 MHz, DMSO d 6 ) δ 158.3, 155.9, 142.7, 132.8, 131.3, 129.3, 126.1, 124.4, 122.7, 121.8, 121.6, 121.0, 120.3, 115.0, 112.7, 63.3, 14.4; MS (ESI): m/z 282 [M + H] + ; HRMS (ESI): m/z calcd for C 17 H 16 O 3 N: ; found: [M + H] +. 6
7 4-(2-Bromophenyl)-3-hydroxyquinolin-2(1H)-one (4h): By following the general procedure, 4h was purified by silica gel chromatography (EA/PE = 25/75). Off white solid; Yield: 245 mg (78%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.48 (s, 1H), 7.80 (dd, J = 8.0, 0.9 Hz, 1H), 7.52 (td, J = 7.4, 1.1 Hz, 1H), 7.41 (td, J = 7.7, 1.7 Hz, 1H), (m, 3H), 7.07 (ddd, J = 8.2, 6.3, 2.1 Hz, 1H), 6.74 (d, J = 7.9 Hz, 1H); 13 C NMR (75 MHz, DMSO d 6 ) δ 158.2, 142.8, 135.0, 133.0, 132.5, 131.7, 129.9, 127.9, 126.4, 123.8, 123.4, 123.2, 122.2, 120.3, 115.2; MS (ESI): m/z 315 [M + H] + ; HRMS (ESI): m/z calcd for C 15 H 11 O 2 NBr: ; found: [M + H] +. 3-Hydroxy-1-methyl-4-phenylquinolin-2(1H)-one (4i): By following the general procedure, 4iwas purified by silica gel chromatography (EA/PE = 10/90). White solid; Yield: 226 mg (90%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ 9.23 (s, 1H), 7.57 (d, J = 8.5 Hz, 1H), (m, 2H), (m, 2H), (m, 2H), (m, 2H), 3.79 (s, 3H); 13 C NMR (75 MHz, DMSO d 6 ) δ 158.0, 141.6, 134.2, 133.6, 129.8, 128.3, 127.7, 126.8, 124.9, 122.9, 122.4, 121.3, 114.7, 29.9; MS (ESI): m/z 252 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 14 O 2 N: ; found: [M + H] +. 3-Hydroxy-4-(4-methoxyphenyl)-1-methylquinolin-2(1H)-one (4j): By following the general procedure, 4j was purified by silica gel chromatography (EA/PE = 15/85). White solid; Yield: 270 mg (96%); mp: o C; 1 H NMR (400 MHz, CDCl 3 ) δ
8 7.40 (m, 3H), (m, 2H), 7.20 (ddd, J = 8.2, 6.8, 1.5 Hz, 1H), 7.13 (s, 1H), (m, 2H), 3.89 (s, 6H); 13 C NMR (101 MHz, CDCl 3 ) δ 159.4, 159.0, 140.9, 134.4, 131.1, 127.2, 126.2, 124.9, 123.0, 122.9, 122.3, 114.1, 114.0, 55.3, 30.4;MS (ESI): m/z 282 [M + H] + ; HRMS (ESI): m/z calcd for C 17 H 16 O 3 N: ; found: [M + H] +. 4-(4-Chlorophenyl)-3-hydroxy-1-methylquinolin-2(1H)-one (4k): By following the general procedure, 4k was purified by silica gel chromatography (EA/PE = 15/85). Off white solid; Yield: 248 mg (87%) mp: o C; 1 H NMR (400 MHz, DMSO d 6 ) δ 9.37 (s, 1H), 7.59 (dt, J = 4.3, 2.4 Hz, 3H), 7.47 (ddd, J = 8.5, 7.1, 1.5 Hz, 1H), (m, 2H), (m, 1H), 7.12 (dd, J = 8.0, 1.4 Hz, 1H), 3.79 (s, 3H); 13 C NMR (101 MHz, DMSO d 6 ) δ 158.4, 142.3, 134.8, 133.0, 132.9, 132.3, 128.9, 127.4, 125.2, 123.1, 122.2, 121.5, 115.3, 30.5; MS (ESI): m/z 286 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 13 O 2 NCl: ; found: [M + H] +. NO 2 OH N O 3-Hydroxy-1-methyl-4-(4-nitrophenyl)quinolin-2(1H)-one (4l): By following the general procedure, 4l was purified by silica gel chromatography (EA/PE = 25/75). Pale yellow solid; Yield: 245 mg (83%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ 9.71 (s, 1H), 8.43 (d, J = 8.6 Hz, 2H), 7.69 (d, J = 8.6 Hz, 2H), 7.65 (d, J = 8.7 Hz, 1H), 7.54 (t, J = 7.5 Hz, 1H), 7.25 (t, J = 7.5 Hz, 1H), 7.12 (d, J = 7.8 Hz, 1H), 3.84 (s, 3H); 13 C NMR (75 MHz, DMSO d 6 ) δ 157.7, 146.9, 141.8, 140.9, 134.2, 131.5, 127.2, 124.4, 123.5, 122.8, 121.0, 120.4, 114.9, 30.0; MS (ESI): m/z 297 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 13 O 4 N 2 : found: [M + H] +. 8
9 4-(2-Bromophenyl)-3-hydroxy-1-methylquinolin-2(1H)-one (4m) By following the general procedure, 4m was purified by silica gel chromatography (EA/PE = 20/80). Off white solid; Yield: 260 mg (79%); mp: o C; 1 H NMR (500 MHz, CDCl 3 ) δ 7.77 (dd, J = 8.0, 1.0 Hz, 1H), (m, 3H), (m, 2H), 7.19 (ddd, J = 8.1, 6.9, 1.4 Hz, 1H), 7.15 (s, 1H), 7.08 (dd, J = 8.0, 1.2 Hz, 1H), 3.91 (s, 3H); 13 C NMR (101 MHz, DMSO d 6 ) δ 158.5, 142.5, 135.4, 134.6, 133.0, 132.2, 130.5, 128.5, 127.4, 124.9, 124.0, 123.2, 122.8, 121.2, 115.3, 30.5; MS (ESI): m/z 330 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 13 O 2 NBr: ; found: [M + H] +. 1-Benzyl-3-hydroxy-4-phenylquinolin-2(1H)-one (4n): By following the general procedure, 4n was purified by silica gel chromatography (EA/PE = 15/85). White solid; Yield: 291 mg (89%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ 9.41 (s, 1H), 7.54 (t, J = 7.2 Hz, 2H), 7.45 (dd, J = 11.1, 7.9 Hz, 2H), (m, 5H), 7.28 (d, J = 7.3 Hz, 3H), 7.13 (d, J = 3.5 Hz, 2H), 5.68 (s, 2H); 13 C NMR (75 MHz, DMSO d 6 ) δ 158.4, 141.5, , 133.6, 133.5, 129.9, 128.6, 128.4, 127.7, 127.1, 126.8, 126.5, 125.1, 123.7, 122.5, 121.7, 115.1, 45.6; MS (ESI): m/z 328 [M + H] + ; HRMS (ESI): m/z calcd for C 22 H 18 O 2 N: ; found: [M + H] +. 9
10 1-Benzyl-3-hydroxy-4-(4-methoxyphenyl)quinolin-2(1H)-one (4o): By following the general procedure, 4o was purified by silica gel chromatography (EA/PE = 20/80). Off white solid; Yield: 335 mg (94%); mp: o C; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), (m, 2H), (m, 4H), 7.28 (dt, J = 4.6, 2.8 Hz, 3H), 7.14 (td, J = 6.7, 1.9 Hz, 2H), (m, 2H), 5.69 (s, 2H), 3.89 (s, 3H); 13 C NMR (101 MHz, CDCl 3 ) δ 159.5, 159.4, 140.8, 135.8, 133.9, 131.2, 128.9, 127.5, 127.3, 126.6, 126.4, 124.9, 123.7, 123.0, 122.5, 115.1, 114.1, 55.3, 47.1; MS (ESI): m/z 357 [M + H] + ; HRMS (ESI): m/z calcd for C 23 H 20 O 3 N: ; found: [M + H] +. 1-Benzyl-4-(4-chlorophenyl)-3-hydroxyquinolin-2(1H)-one (4p): By following the general procedure, 4p was purified by silica gel chromatography (EA/PE = 20/80). White solid; Yield: 310 mg (86%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ 9.50 (s, 1H), 7.54 (d, J = 7.5 Hz, 2H), (m, 9H), 7.06 (s, 2H), 5.61 (s, 2H); 13 C NMR (101 MHz, DMSO d 6 ) δ 158.8, 142.3, 136.9, 134.0, 133.0, 133.0, 132.4, 129.2, 129.0, 127.6, 127.4, 127.0, 125.5, 123.2, 123.0, 121.9, 115.7, 46.1; MS (ESI): m/z 362 [M + H] + ; HRMS (ESI): m/z calcd for C 22 H 17 O 2 NCl: ; found: [M + H] +. 1-Benzyl-3-hydroxy-4-(4-nitrophenyl)quinolin-2(1H)-one (4q): By following the general procedure, 4q was purified by silica gel chromatography (EA/PE = 30/70). Off white solid, Yield: 297 mg (80%); mp: o C; 1 H NMR (400 MHz, DMSO d 6 ) δ 9.69 (s, 1H), 8.39 (d, J = 7.9 Hz, 2H), 7.69 (d, J = 7.8 Hz, 2H), 7.43 (d, J = 8.1 Hz, 1H),
11 7.22 (m, 6H), 7.12 (d, J = 3.6 Hz, 2H), 5.69 (s, 2H); 13 C NMR (75 MHz, DMSO d 6 + CDCl 3 ) δ 158.2, 146.9, 141.9, 140.9, 136.3, 133.5, 131.5, 128.6, 127.1, 126.9, , 124.7, 123.4, 122.7, 121.6, 120.8, 115.3, 45.7; MS (ESI): m/z 373 [M + H] + ; HRMS (ESI): m/z calcd for C 22 H 17 O 4 N 2 : ; found: [M + H] +. OH 3-Hydroxy-4-(3-hydroxyphenyl)quinolin-2(1H)-one or Viridicatol (4r or III): N H By following the general procedure, IV was purified by silica gel chromatography (EA/PE = 35/65). White solid; Yield: 184 mg (73%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.54 (s, 1H), 9.18 (s, 1H), (m, 3H), 7.09 (s, 2H), 6.82 (d, J = 7.4 Hz, 1H), 6.72 (d, J = 6.5 Hz, 2H); 13 C NMR (75 MHz, DMSO d 6 ) δ 158.2, 157.2, 142.1, 134.8, 133.0, 129.3, 126.3, 124.4, 124.0, 122.0, 120.8, 120.3, 116.6, , 114.5; MS (ESI): m/z 284 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 14 O 4 N: ; found: [M + H] +. N OH O OH 3-Hydroxy-4-(pyridin-4-yl)quinolin-2(1H)-one (4s): N H By following the general procedure, 4s was purified by silica gel chromatography (MeOH/EA = 5/95). Off white solid, Yield: 190 mg (80%); mp: o C; 1 H NMR (400 MHz, DMSO d 6 ) δ (s, 1H), 9.59 (s, 1H), 8.72 (d, J = 5.8 Hz, 2H), 7.39 (d, J = 5.9 Hz, 2H), 7.37 (d, J = 2.7 Hz, 2H), 7.11 (ddd, J = 8.2, 5.4, 2.9 Hz, 1H), 7.02 (d, J = 8.0 Hz, 1H); 13 C NMR (75 MHz, DMSO d 6 ) δ 157.9, 149.7, 142.6, 141.9, 133.1, 126.7, 125.0, 123.7, 122.4, 121.3, 119.7, 115.4; MS (ESI): m/z 239 [M + H] + ; HRMS (ESI): m/z calcd for C 14 H 11 O 2 N 2 : ; found: [M + H] +. O 11
12 3-Hydroxy-4-(thiophen-2-yl)quinolin-2(1H)-one (4t): By following the general procedure, 4t was purified by silica gel chromatography (EA/PE = 30/70). Off white solid, Yield: 211 mg (87%); mp: o C; 1 H NMR (400 MHz, DMSO d 6 ) δ (s, 1H), 9.67 (s, 1H), 7.76 (dd, J = 5.1, 1.1 Hz, 1H), 7.40 (d, J = 8.0 Hz, 1H), 7.35 (d, J = 3.7 Hz, 2H), 7.24 (dd, J = 5.1, 3.5 Hz, 1H), 7.20 (dd, J = 3.5, 1.1 Hz, 1H), (m, 1H); 13 C NMR (101 MHz, DMSO d 6 ) δ 158.2, 144.3, 133.7, 133.4, 129.3, 127.6, 127.5, 127.1, 124.7, 122.8, 121.2, 117.1, 115.8; MS (ESI): m/z 244 [M + H] + ; HRMS (ESI): m/z calcd for C 13 H 10 O 2 NS: ; found: [M + H] +. 3-Hydroxy-6-methoxy-4-phenylquinolin-2(1H)-one (5a): By following the general procedure, 5a was purified by silica gel chromatography (EA/PE = 30/70). White solid; Yield: 235 mg (88%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.20 (s, 1H), 7.52 (t, J = 7.2 Hz, 2H), 7.44 (t, J = 7.3 Hz, 1H), (m, 2H), 7.29 (d, J = 8.9 Hz, 1H), 7.01 (dd, J = 8.9, 2.7 Hz, 1H), 6.51 (d, J = 2.7 Hz, 1H), 3.59 (s, 3H). 13 C NMR (75 MHz, DMSO d 6 ) δ 157.7, 154.4, 142.9, 133.7, 129.7, 128.3, 127.6, 127.5, 123.4, 121.7, 116.4, 114.3, 107.2, 55.1; MS (ESI): m/z 268 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 14 O 3 N: ; found: [M + H] +. 3-Hydroxy-6-methoxy-4-(4-methoxyphenyl)quinolin-2(1H)-one (5b): By following the general procedure, 58 was purified by silica gel chromatography (EA/PE = 35/65). Off white solid, Yield: 282 mg (95%) mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.10 (s, 1H), 7.28 (d, J = 8.0 Hz, 3H), 7.07 (d, J = 8.5 Hz, 2H), 7.00 (d, J = 8.8 Hz, 2H), 6.59 (s, 1H), 3.82 (s, 3H), 3.61 (s, 3H); 13 C NMR (75 MHz, DMSO d 6 ) δ 158.6, 157.7, 154.4, 142.9, 131.0, 127.5, 125.5, 123.1, 121.9, 116.4, 114.3, 113.7, 107.3, 55.1, 55.0; MS (ESI): 12
13 m/z 298 [M + H] + ; HRMS (ESI): m/z calcd for C 17 H 16 O 4 N: ; found: [M + H] +. 4-(4-Chlorophenyl)-3-hydroxy-6-methoxyquinolin-2(1H)-one (5c): By following the general procedure, 5c was purified by silica gel chromatography (EA/PE = 30/70). White solid; Yield: 262 mg (87%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.39 (s, 1H), 7.58 (d, J = 8.4 Hz, 2H), 7.39 (d, J = 8.4 Hz, 2H), 7.29 (d, J = 8.9 Hz, 1H), 7.01 (dd, J = 8.9, 2.7 Hz, 1H), 6.49 (d, J = 2.6 Hz, 1H), 3.61 (s, 3H); 13 C NMR (75 MHz, DMSO d 6 ) δ 157.5, 154.5, 143.1, 132.5, 132.4, 131.7, 128.4, 127.5, 122.2, 121.3, 116.5, 114.5, 106.8, 55.1; MS (ESI): m/z 302 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 13 O 3 NCl: ; found: [M + H] +. NO 2 O OH 3-Hydroxy-6-methoxy-4-(4-nitrophenyl)quinolin-2(1H)-one (5d): By following the general procedure, 5d was purified by silica gel chromatography (EA/PE = 40/60). Yellow solid; Yield: 249 mg (80%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.61 (s, 1H), 8.31 (d, J = 8.2 Hz, 2H), 7.61 (d, J = 8.1 Hz, 2H), 7.25 (d, J = 8.6 Hz, 1H), 6.97 (d, J = 7.7 Hz, 1H), 6.39 (s, 1H), 3.54 (s, 3H); 13 C NMR (75 MHz, DMSO d 6 ) δ 157.3, 154.6, 146.9, 143.3, 141.0, 131.4, 127.5, 123.5, 121.4, , 116.6, 114.7, 106.6, 55.2; MS (ESI): m/z 313 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 13 O 5 N 2 : ; found: [M + H] +. N H O 13
14 6-Chloro-3-hydroxy-4-phenylquinolin-2(1H)-one (5e): By following the general procedure, 5e was purified by silica gel chromatography (EA/PE = 30/70). White solid; Yield: 230 mg (85%); mp: ; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.55 (s, 1H), 7.54 (t, J = 7.2 Hz, 2H), 7.47 (d, J = 7.1 Hz, 1H), 7.35 (dd, J = 6.3, 4.8 Hz, 4H), 6.94 (s, 1H); 13 C NMR (101 MHz, DMSO d 6 ) δ 158.0, 143.5, 133.0, 131.8, 129.7, 128.5, 127.9, 126.2, 126.1, 122.9, 122.8, 122.4, 117.1; MS (ESI): m/z 272 [M + H] + ; HRMS (ESI): m/z calcd for C 15 H 11 O 2 NCl: ; found: [M + H] +. 6-Chloro-3-hydroxy-4-(4-methoxyphenyl)quinolin-2(1H)-one (5f): By following the general procedure, 5f was purified by silica gel chromatography (EA/PE = 35/65). White solid; Yield: 271 mg (90%) mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.39 (s, 1H), (m, 2H), 7.21 (d, J = 8.6 Hz, 2H), 7.02 (d, J = 8.6 Hz, 2H), 6.96 (s, 1H), 3.77 (s, 3H); 13 C NMR (75 MHz, DMSO d 6 ) δ 158.8, 158.0, 143.5, 131.8, 131.0, 126.1, 124.9, 123.1, 122.7, 122.7, 117.1, 113.9, 55.0; MS (ESI): m/z 302 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 13 O 3 NCl: ; found: [M + H] +. 6-Chloro-4-(4-chlorophenyl)-3-hydroxyquinolin-2(1H)-one (5g) By following the general procedure, 5g was purified by silica gel chromatography (EA/PE = 35/65). Off white solid; Yield: 244 mg (80%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.65 (s, 1H), 7.53 (d, J = 8.4 Hz, 2H), 7.31 (dd, J = 10.3, 6.1 Hz, 4H), 6.87 (d, J = 1.6 Hz, 1H); 13 C NMR (75 MHz, DMSO d 6 ) δ 157.9, 143.7, 132.7, 131.9, 131.8, 131.7, 128.6, 126.3, 122.7, 122.1, 121.6, 117.1; MS (ESI): m/z 306 [M + H] + ; HRMS (ESI): m/z calcd for C 15 H 10 O 2 NCl 2 : ; found: [M + H] +. 14
15 6-Chloro-3-hydroxy-4-(4-nitrophenyl)quinolin-2(1H)-one (5h): By following the general procedure, 5h was purified by silica gel chromatography (EA/PE = 45/55). Pale yellow solid; Yield: 246 mg (78%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), 9.97 (s, 1H), 8.38 (d, J = 8.7 Hz, 2H), 7.66 (d, J = 8.6 Hz, 2H), (m, 2H), 6.92 (s, 1H); 13 C NMR (101 MHz, DMSO d 6 ) δ 158.2, 147.6, 144.4, 140.8, 132.4, 131.9, 127.0, 126.9, 124.2, 123.1, 122.0, 121.4, 117.7; MS (ESI): m/z 317 [M + H] + ; HRMS (ESI): m/z calcd for C 15 H 9 O 4 N 2 Cl: ; found: [M + H] +. 3-Hydroxy-6-nitro-4-phenylquinolin-2(1H)-one (5i): By following the general procedure, 5i was purified by silica gel chromatography (EA/PE = 35/65). Yellow solid; Yield: 216 mg (77%); mp: o C; 1 H NMR (400 MHz, DMSO d 6 ) δ (s, 1H), 9.88 (s, 1H), 8.19 (dd, J = 9.0, 2.5 Hz, 1H), 7.90 (d, J = 2.5 Hz, 1H), 7.58 (t, J = 7.3 Hz, 2H), 7.51 (dt, J = 7.3, 2.7 Hz, 2H), (m, 2H); 13 C NMR (75 MHz, DMSO d 6 ) δ 158.5, 144.0, 141.9, 137.7, 132.6, 129.8, 128.6, 128.2, 123.4, 121.2, 121.0, 120.0, 116.2; MS (ESI): m/z 283 [M + H] + ; HRMS (ESI): m/z calcd for C 15 H 11 O 4 N 2 : ; found: [M + H] +. 3-Hydroxy-4-(4-methoxyphenyl)-6-nitroquinolin-2(1H)-one (5j): By following the general procedure, 5j was purified by silica gel chromatography (EA/PE = 40/60). Yellow solid; Yield: 259 mg (83%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ 15
16 12.78 (s, 1H), 9.81 (s, 1H), 8.18 (d, J = 9.0 Hz, 1H), 7.97 (s, 1H), 7.49 (d, J = 8.9 Hz, 1H), 7.33 (d, J = 8.4 Hz, 2H), 7.12 (d, J = 8.4 Hz, 2H), 3.85 (s, 3H); 13 C NMR (101 MHz, DMSO d 6 ) δ 159.5, 159.0, 144.6, 142.4, 138.2, 131.6, 124.9, 123.8, 121.8, 120.7, 116.7, 114.5, 55.6; MS (ESI): m/z 313 [M + H] + ; HRMS (ESI): m/z calcd for C 16 H 13 O 5 N 2 : ; found: [M + H] +. 4-(4-Chlorophenyl)-3-hydroxy-6-nitroquinolin-2(1H)-one (5k) By following the general procedure, 5k was purified by silica gel chromatography (EA/PE = 45/55). Yellow solid; Yield: 253 mg (80%); mp: o C; 1 H NMR (300 MHz, DMSO d 6 ) δ (s, 1H), (s, 1H), 8.19 (dd, J = 9.0, 2.4 Hz, 1H), 7.86 (d, J = 2.3 Hz, 1H), 7.64 (d, J = 8.4 Hz, 2H), 7.50 (d, J = 9.0 Hz, 1H), 7.44 (d, J = 8.4 Hz, 2H); 13 C NMR (75 MHz, DMSO d 6 ) δ 158.3, 144.3, 141.9, 137.7, 133.0, 131.8, 131.4, 128.7, 122.2, 121.3, 120.6, 119.7, 116.2; MS (ESI): m/z 317 [M + H] + ; HRMS (ESI): m/z calcd for C 15 H 10 O 4 N 2 Cl: ; found: [M + H] +. 3-Hydroxy-6-nitro-4-(4-nitrophenyl)quinolin-2(1H)-one (5l): By following the general procedure, 5l was purified by silica gel chromatography (EA/PE = 55/45). Yellow solid; Yield: 235 mg (72%); mp: o C; 1 H NMR (400 MHz, DMSO d 6 ) δ (s, 1H), (s, 1H), 8.42 (d, J = 7.6 Hz, 2H), 8.22 (d, J = 8.9 Hz, 1H), 7.83 (s, 1H), 7.73 (d, J = 7.5 Hz, 2H), 7.53 (d, J = 8.9 Hz, 1H); 13 C NMR (75 MHz, DMSO d 6 ) δ 158.2, 147.2, 144.5, 142.0, 139.7, 137.7, 131.5, 123.8, 121.5, 121.4, 120.1, 119.5, 116.3; MS (ESI): m/z 328 [M + H] + ; HRMS (ESI): m/z calcd for C 15 H 10 O 6 N 3 : ; found: [M + H] +. 16
17 4-(4-Chlorophenyl)-8-fluoro-3-hydroxyquinolin-2(1H)-one (5m): The compound 5m was prepared by following the general procedure by taking 4- chlorobenzaldehyde (30 mg, 0.21 mmol), p-toluenesulfonyl hydrazide (39 mg, 0.21 mmol), 7- fluoroisatin (35 mg, 0.21 mmol) and K 2 CO 3 (59 mg, 0.42 mmol) and purified by silica gel chromatography (EA/PE = 25/75). White solid; Yield: 50 mg (81%); mp: o C; 1 H NMR (500 MHz, DMSO d 6 ) δ (s, 1H), 9.65 (s, 1H), 7.58 (d, J = 8.4 Hz, 2H), 7.38 (d, J = 8.4 Hz, 2H), 7.25 (dd, J = 10.2, 8.3 Hz, 1H), 7.07 (td, J = 8.1, 5.3 Hz, 1H), 6.86 (d, J = 8.1 Hz, 1H); 13 C NMR (126 MHz, DMSO d 6 ) δ 158.5, (d, J = Hz), 133.0, 132.8, 132.2, 128.9, (d, J = 3.0 Hz), (d, J = 2.6 Hz), (d, J = 7.4 Hz), (d, J = 13.9 Hz), (d, J = 3.1 Hz); MS (ESI): m/z 290 [M + H] + ; HRMS (ESI): m/z calcd for C 14 H 10 O 2 N 2 FCl: ; found: [M + H] +. 3-Hydroxy-6,8-dimethyl-4-phenylquinolin-2(1H)-one (5n): The compound 5n was prepared by following the general procedure by taking benzaldehyde (30 mg, 0.28 mmol), p-toluenesulfonyl hydrazide (52 mg, 0.28 mmol), 5,7-dimethylisatin (49 mg, 0.28 mmol) and K 2 CO 3 (78 mg, 0.56 mmol) and purified by silica gel chromatography (EA/PE = 20/80). White solid; Yield: 62 mg (83%); mp: o C; 1 H NMR (500 MHz, DMSO d 6 ) δ (s, 1H), 9.11 (s, 1H), 7.48 (dd, J = 31.0, 6.6 Hz, 3H), 7.31 (d, J = 6.3 Hz, 2H), 7.02 (s, 1H), 6.68 (s, 1H), 2.45 (s, 3H), 2.17 (s, 3H); 13 C NMR (126 MHz, DMSO d 6 ) δ 159.0, 142.6, 134.6, 131.0, 130.2, 130.0, 129.8, 128.7, 128.0, 124.7, 123.8, 122.6, 121.5, 21.0, 17.9; MS (ESI): m/z 266 [M + H] + ; HRMS (ESI): m/z calcd for C 17 H 16 O 2 N: ; found: [M + H] +. 17
18 4-(4-Chlorophenyl)-3-hydroxy-6,8-dimethylquinolin-2(1H)-one (5o): The compound 5o was prepared by following the general procedure by taking 4- chlorobenzaldehyde (30 mg, 0.21 mmol), p-toluenesulfonyl hydrazide (39 mg, 0.21 mmol), 5,7- dimethylisatin (37 mg, 0.21 mmol) and K 2 CO 3 (59 mg, 0.42 mmol) purified by silica gel chromatography (EA/PE = 25/75). White solid; Yield: 50 mg (79%); mp: o C; 1 H NMR (500 MHz, DMSO d 6 ) δ (s, 1H), 9.28 (s, 1H), 7.57 (d, J = 8.4 Hz, 2H), 7.34 (d, J = 8.3 Hz, 2H), 7.03 (s, 1H), 6.67 (s, 1H), 2.44 (s, 3H), 2.18 (s, 3H); 13 C NMR (126 MHz, DMSO d 6 ) δ 158.8, 142.8, 133.5, 132.8, 132.2, 131.2, 130.0, 129.9, 128.9, 123.9, 123.5, 122.4, 121.1, 21.0, 17.8; MS (ESI): m/z 300 [M + H] + ; HRMS (ESI): m/z calcd for C 17 H 15 O 2 NCl: ; found: [M + H] +. 5,6-Dichloro-3-hydroxy-4-phenylquinolin-2(1H)-one (5p): The compound 5p was prepared by following the general procedure by taking benzaldehyde (30 mg, 0.28 mmol), p-toluenesulfonyl hydrazide (52 mg, 0.28 mmol), 4,5-dichlorolisatin (61 mg, 0.28 mmol) and K 2 CO 3 (78 mg, 0.56 mmol) and purified by silica gel chromatography (EA/PE = 35/65). Off white solid; Yield: 60 mg (70%); mp: o C; 1 H NMR (500 MHz, DMSO d 6 ) δ (s, 1H), 9.63 (s, 1H), 7.57 (d, J = 8.7 Hz, 1H), (m, 4H), 7.22 (d, J = 6.8 Hz, 2H); 13 C NMR (126 MHz, DMSO d 6 ) δ 157.5, 146.3, 136.5, 134.0, 130.0, 128.1, 127.8, 127.7, 127.6, 127.1, 123.6, 119.8, 116.4; MS (ESI): m/z 306 [M + H] + ; HRMS (ESI): m/z calcd for C 15 H 10 O 2 NCl 2 : ; found: [M + H] +. 18
19 3-Methoxy-1-methyl-4-phenylquinolin-2(1H)-one (6): To a stirred solution of viridicatin (4a, 110 mg, 0.42 mmol) in THF:H 2 O (1:1) was added NaOH (34 mg, 0.84 mmol) and dimethyl sulfate (106 mg, 0.84 mmol), the resulting mixture was stirred at room temperature for 12 h. After completion of the reaction monitored by TLC, the reaction mixture was concentrated under reduced pressure and diluted with water, extracted with DCM. The organic layer was washed with brine, dried over anhydrous Na 2 SO 4, and evaporated to afford crude product. The residue was purified by silica gel chromatography (EA/PE = 30/70). White solid; Yield: 107 mg (96%); mp: o C; Mp: o C; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), (m, 1H), (m, 1H), 7.24 (dd, J = 8.1, 1.4 Hz, 1H), 7.13 (ddd, J = 8.1, 7.1, 1.1 Hz, 1H), 3.83 (s, 1H), 3.76 (s, 1H); 13 C NMR (101 MHz, CDCl 3 ) δ 159.3, 145.1, 137.3, 137.1, 133.5, 129.5, 128.9, 128.4, 128.1, 127.4, 122.3, 121.3, 114.0, 60.2, 29.9; MS (ESI): m/z 266 [M + H] + ; HRMS (ESI): m/z calcd for C 17 H 16 O 2 N: ; found: [M + H] +. 2-Oxo-4-phenyl-1,2-dihydroquinolin-3-yl acetate (7): To mixture of viridicatin (4a, 100 mg 0.42 mmol) and Et 3 N (87 µl, 0.63 mmol) in DCM, acetyl chloride (30 µl, 0.42 mmol) was added at 0 o C. Then the reaction mixture was allowed to stir at room temperature for 4 h. After completion of the reaction monitored by TLC, the reaction mixture was diluted with water and extracted with DCM. The organic layer was washed with brine, dried over anhydrous Na 2 SO 4, and evaporated to afford the crude product, which was purified by silica gel chromatography (EA/PE = 25/75). White solid; Yield: 109 mg (93%); mp: o C; 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), (m, 4H), 7.44 (d, J = 8.0 Hz, 1H), (m, 2H), (m, 1H), 7.15 (t, J = 7.5 Hz, 1H), 2.17 (s, 3H); 13 C NMR (101 MHz, CDCl 3 ) δ 168.9, 159.0, 141.9, 137.3, 136.5, 132.3, 130.1, 128.9, 128.7, 128.5, 126.8, 122.9, 120.0, 116.4, 20.4; 19
20 MS (ESI): m/z 280 [M + H] + ; HRMS (ESI): m/z calcd for C 17 H 14 O 3 N: ; found: [M + H] +. (E)-N'-Benzylidene-4-methylbenzenesulfonohydrazide (8): A mixture of benzaldehyde (106 mg, 1 mmol) and p-toluenesulfonyl hydrazide (186 mg, 1 mmol) in ethanol was stirred at room temperature for 1 h. After the reaction was finished monitored by TLC, the solvent was evaporated under reduced pressure and dried in vacuum to afford the desired product as White solid; Yield: 264 mg (96%); mp: o C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.98 (s, 1H), (m, 2H), 7.76 (s, 1H), (m, 2H), 7.36 (ddd, J = 5.5, 3.5, 1.7 Hz, 3H), 7.31 (d, J = 8.0 Hz, 2H), 2.41 (s, 3H); 13 C NMR (101 MHz, CDCl 3 ) δ 148.1, 144.3, 135.2, 133.2, 130.3, 129.7, 128.6, 127.9, 127.4, 21.6; MS (ESI): m/z 275 [M + H] + ; HRMS (ESI): m/z calcd for C 14 H 15 O 2 N 2 S: ; found: [M + H] +. 20
21 3-Hydroxy-4-phenylquinolin-2(1H)-one or Viridicatin (4a or II): OH N O H 4a 1 H NMR, 300 MHz 21
22 3-Hydroxy-4-(4-methoxyphenyl)quinolin-2(1H)-one (4b)
23 23 3-Hydroxy-4-(3-methoxyphenyl)quinolin-2(1H)-one (4c): f1 (ppm) f1 (ppm)
24 3-Hydroxy-4-(2-methoxyphenyl)quinolin-2(1H)-one (4d): 24
25 4-(4-Chlorophenyl)-3-hydroxyquinolin-2(1H)-one (4e): 25
26 3-Hydroxy-4-(4-nitrophenyl)quinolin-2(1H)-one (4f): 26
27 27 4-(2-Ethoxyphenyl)-3-hydroxyquinolin-2(1H)-one (4g): f1 (ppm) f1 (ppm)
28 4-(2-Bromophenyl)-3-hydroxyquinolin-2(1H)-one (4h): 28
29 3-Hydroxy-1-methyl-4-phenylquinolin-2(1H)-one (4i): 29
30 3-Hydroxy-4-(4-methoxyphenyl)-1-methylquinolin-2(1H)-one (4j): 30
31 4-(4-Chlorophenyl)-3-hydroxy-1-methylquinolin-2(1H)-one (4k): 31
32 32 3-Hydroxy-1-methyl-4-(4-nitrophenyl)quinolin-2(1H)-one (4l): f1 (ppm) f1 (ppm)
33 4-(2-Bromophenyl)-3-hydroxy-1-methylquinolin-2(1H)-one (4m):
34 1-Benzyl-3-hydroxy-4-phenylquinolin-2(1H)-one (4n):
35 35 1-Benzyl-3-hydroxy-4-(4-methoxyphenyl)quinolin-2(1H)-one (4o):
36 1-Benzyl-4-(4-chlorophenyl)-3-hydroxyquinolin-2(1H)-one (4p): 36
37 1-Benzyl-3-hydroxy-4-(4-nitrophenyl)quinolin-2(1H)-one (4q): 37
38 3-Hydroxy-4-(3-hydroxyphenyl)quinolin-2(1H)-one or Viridicatol ( 4r or III): 38
39 39 3-Hydroxy-4-(pyridin-4-yl)quinolin-2(1H)-one (4s): f1 (ppm) f1 (ppm)
40 40 3-Hydroxy-4-(thiophen-2-yl)quinolin-2(1H)-one (4t): f1 (ppm) f1 (ppm)
41 3-Hydroxy-6-methoxy-4-phenylquinolin-2(1H)-one (5a): 41
42 42 3-Hydroxy-6-methoxy-4-(4-methoxyphenyl)quinolin-2(1H)-one (5b): f1 (ppm) f1 (ppm)
43 4-(4-Chlorophenyl)-3-hydroxy-6-methoxyquinolin-2(1H)-one (5c):
44 3-Hydroxy-6-methoxy-4-(4-nitrophenyl)quinolin-2(1H)-one (5d): 44
45 45 6-Chloro-3-hydroxy-4-phenylquinolin-2(1H)-one (5e): f1 (ppm) f1 (ppm)
46 46 6-Chloro-3-hydroxy-4-(4-methoxyphenyl)quinolin-2(1H)-one (5f): f1 (ppm) f1 (ppm)
47 6-Chloro-4-(4-chlorophenyl)-3-hydroxyquinolin-2(1H)-one (5g): 47
48 48 6-Chloro-3-hydroxy-4-(4-nitrophenyl)quinolin-2(1H)-one (5h) f1 (ppm) f1 (ppm)
49 49 3-Hydroxy-6-nitro-4-phenylquinolin-2(1H)-one (5i): f1 (ppm) f1 (ppm)
50 3-Hydroxy-4-(4-methoxyphenyl)-6-nitroquinolin-2(1H)-one (5j): 50
51 4-(4-Chlorophenyl)-3-hydroxy-6-nitroquinolin-2(1H)-one (5k): 51
52 3-Hydroxy-6-nitro-4-(4-nitrophenyl)quinolin-2(1H)-one (5l): 52
53 4-(4-Chlorophenyl)-8-fluoro-3-hydroxyquinolin-2(1H)-one (5m): Cl OH N O H F 5m 1 H NMR, 500 MHz 53
54 3-Hydroxy-6,8-dimethyl-4-phenylquinolin-2(1H)-one (5n): OH N H O 5n 1 H NMR, 500 MHz OH N H O 5n 13 C NMR, 126 MHz f1 (ppm)
55 4-(4-Chlorophenyl)-3-hydroxy-6,8-dimethylquinolin-2(1H)-one (5o): 55
56 5,6-Dichloro-3-hydroxy-4-phenylquinolin-2(1H)-one (5p): Cl Cl OH N H O 5p 1 H NMR, 500 MHz f1 (ppm)
57 57 3-Methoxy-1-methyl-4-phenylquinolin-2(1H)-one (6): f1 (ppm) f1 (ppm) f1 (ppm)
58 4-(2-Bromophenyl)-3-hydroxy-1-methylquinolin-2(1H)-one (7): 58
59 (E)-N'-Benzylidene-4-methylbenzenesulfonohydrazide (8): 59
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