Journal Information
Journal ID (publisher-id): chemical
Title: Journal of the Korean Chemical Society
Translated Title (ko): 대한화학회지
ISSN (print): 1017-2548
ISSN (electronic): 2234-8530
Publisher: Korean Chemical Society대한화학회
Spectral data of thioflavones and their pyridyl analogs
Thioflavone (9a): mp 125-126 °C; 1H NMR (300 MHz, CDCl3) δ 8.55 (d, J = 7.5 Hz, 1H), 7.62-7.71 (m, 4H), 7.55-7.61 (m, 1H), 7.48-7.55 (m, 3H), 7.24 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 180.9, 153.1, 137.7, 136.6, 131.6, 130.9, 130.8, 129.3, 128.6, 127.8, 127.0, 126.5, 123.5; FT-IR (KBr) 1615 (C=O) cm−1; Ms m/z (%) 238 (M+, 100).
2’-Methoxythioflavone (9b): mp 131-132 °C; 1H NMR (300 MHz, CDCl3) δ 8.57 (d, J = 8.4 Hz, 1H), 7.61-7.64 (m, 2H), 7.51-7.59 (m, 1H), 7.42-7.49 (m, 2H), 7.18 (s, 1H), 7.01-7.10 (m, 2H), 3.88 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 180.8, 156.5, 150.3, 138.8, 131.6, 131.3, 130.9, 130.3, 128.5, 127.5, 126.8, 126.2, 125.5, 120.9, 111.7, 55.8; FT-IR (KBr) 1614 (C=O) cm−1; Ms m/z (%) 268 (M+, 100).
3’-Chlorothioflavone (9c): mp 144-145 °C; 1H NMR (300 MHz, CDCl3) δ 8.56 (d, J = 7.6 Hz, 1H), 7.63-7.71 (m, 3H), 7.55-7.61 (m, 2H), 7.49-7.53 (m, 1H), 7.43-7.49 (m, 1H), 7.23 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 180.7, 151.3, 138.3, 137.3, 135.3, 131.8, 130.8 (overlapped), 130.6, 128.7, 128.0, 127.1, 126.6, 125.1, 123.9; FT-IR (KBr) 1620 (C=O) cm−1; Ms m/z (%) 274 (M++2, 35), 272 (M+, 100).
4’-Bromothioflavone (9d): mp 169-170 °C; 1H NMR (300 MHz, CDCl3) δ 8.55 (d, J = 7.7 Hz, 1H), 7.65 (d, J = 8.5 Hz, 2H), 7.63-7.67 (m, 2H), 7.57 (d, J = 8.5 Hz, 2H), 7.54-7.60 (m, 1H), 7.21 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 180.7, 151.6, 137.3, 125.4, 132.5, 131.8, 130.8, 128.6, 128.4, 128.0, 126.5, 125.4, 123.5; FT-IR (KBr) 1615 (C=O) cm−1; Ms m/z (%) 318 (M++2, 99), 316 (M+, 100).
4’-Methoxythioflavone (9f): mp 125-126 °C; 1H NMR (300 MHz, CDCl3) δ 8.55 (d, J = 7.5 Hz, 1H), 7.67 (d, J = 8.9 Hz, 2H), 7.59-7.68 (m, 2H), 7.52-7.58 (m, 1H), 7.22 (s, 1H), 7.02 (d, J = 8.9 Hz, 2H), 3.89 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 180.9, 161.8, 152.8, 137.6, 131.5, 130.9, 128.8, 128.5, 128.3, 127.7, 126.4, 122.2, 114.7, 55.5; FT-IR (KBr) 1625 (C=O) cm−1; Ms m/z (%) 268 (M+, 100).
2-(3-Pyridyl)-4H-1-benzothiopyran-4-one (9g): mp 162-164 °C; 1H NMR (300 MHz, CDCl3) δ 8.95 (d, J = 2.2 Hz, 1H), 8.77 (d, J = 4.8 Hz, 1H), 8.56 (d, J = 8.0 Hz, 1H), 7.96-8.01 (m, 1H), 7.63-7.71 (m, 2H), 7.55-7.62 (m, 1H), 7.47 (dd, J = 8.0, 4.8 Hz, 1H), 7.23 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 180.5, 151.7, 149.4, 147.7, 137.2, 134.4, 132.6, 131.9, 130.8, 128.7, 128.1, 126.6, 124.3, 123.9; FT-IR (KBr) 1618 (C=O) cm−1; Ms m/z (%) 239 (M+, 100).
2-Phenyl-4H-thiopyrano[2,3-b]pyridin-4-one (10a): mp 121-123 °C; 1H NMR (300 MHz, CDCl3) δ 8.82 (dd, J = 4.5, 1.9 Hz, 1H), 8.77 (dd, J = 8.1, 1.9 Hz, 1H), 7.68-7.74 (m, 2H), 7.49-7.52 (m, 4H), 7.27 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 181.3, 159.1, 154.8, 152.8, 136.8, 136.3, 131.1, 129.4, 128.1, 127.0, 123.6, 123.0; FT-IR (KBr) 1617 (C=O) cm−1; Ms m/z (%) 239 (M+, 100).
2-(2’-Methoxyphenyl)-4H-thiopyrano[2,3-b]pyridin-4-one (10b): mp 118-119 °C; 1H NMR (300 MHz, CDCl3) δ 8.76-8.81 (m, 2H), 7.44-7.52 (m, 3H), 7.20 (s, 1H), 7.02-7.11 (m, 2H), 3.89 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 181.4, 159.9, 156.4, 152.6, 152.1, 136.6, 131.8, 130.2, 128.1, 126.8, 125.2, 122.6, 121.0, 111.8, 55.8; FT-IR (KBr) 1616 (C=O) cm−1; Ms m/z (%) 269 (M+, 100).
2-(3’-Chlorophenyl)-4H-thiopyrano[2,3-b]pyridin-4-one (10c): mp 188-190 °C; 1H NMR (300 MHz, CDCl3) δ 8.84 (dd, J = 4.4, 1.5 Hz, 1H), 8.78 (dd, J = 8.1, 1.4 Hz, 1H), 7.68-7.71 (m, 1H), 7.57-7.62 (m, 1H), 7.45-7.52 (m, 3H), 7.24 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 181.2, 158.8, 153.1, 153.0, 138.0, 136.8, 135.5, 131.1, 130.7, 128.0, 127.1, 125.2, 124.1, 123.1; FT-IR (KBr) 1620 (C=O) cm−1; Ms m/z (%) 275 (M++2, 38), 273 (M+, 100).
2-(4’-Methylphenyl)-4H-thiopyrano[2,3-b]pyridin-4-one (10e): mp 163-164 °C; 1H NMR (300 MHz, CDCl3) δ 8.81 (dd, J = 4.5, 1.7 Hz, 1H), 8.77 (dd, J = 8.1, 1.8 Hz, 1H), 7.62 (d, J = 8.2 Hz, 2H), 7.51 (dd, J = 8.1, 4.5 Hz, 1H), 7.34 (d, J = 8.0 Hz, 2H), 7.26 (s, 1H), 2.45 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 181.4, 159.1, 154.8, 152.7, 141.7, 136.7, 133.4, 130.1, 128.1, 126.8, 122.9 (overlapped), 21.4; FT-IR (KBr) 1616 (C=O) cm−1; Ms m/z (%) 253 (M+, 100).
2-(4’-Methoxyphenyl)-4H-thiopyrano[2,3-b]pyridin-4-one (10f): mp 160-161 °C; 1H NMR (300 MHz, CDCl3) δ 8.80 (dd, J = 4.6, 1.9 Hz, 1H), 8.76 (dd, J = 8.1, 1.9 Hz, 1H), 7.68 (d, J = 8.9 Hz, 2H), 7.50 (dd, J = 8.0, 4.6 Hz, 1H), 7.23 (s, 1H), 7.04 (d, J = 8.9 Hz, 2H), 3.89 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 181.3, 162.1, 159.0, 154.4, 152.7, 136.7, 128.5, 128.4, 128.0, 122.8, 122.2, 114.8, 55.6; FT-IR (KBr) 1615 (C=O) cm−1; Ms m/z (%) 269 (M+, 100).
2-(3-Thienyl)-4H-thiopyrano[2,3-b]pyridin-4-one (10h): mp 179-180 °C; 1H NMR (300 MHz, CDCl3) δ 8.80 (dd, J = 4.5, 1.8 Hz, 1H), 8.84 (dd, J = 8.1, 1.9 Hz, 1H), 7.84 (dd, J = 2.8, 1.4 Hz, 1H), 7.45-7.53 (m, 3H), 7.27 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 181.5, 158.6, 152.8, 148.4, 137.4, 136.6, 128.2, 127.8, 125.6, 125.2, 122.9, 122.0; FT-IR (KBr) 1621 (C=O) cm−1; Ms m/z (%) 245 (M+, 100).