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Y. Peng et al.
PAPER
2-p-Tolyl-4-p-tolylsulfanylquinazoline (7h)
Yield: 27.1 mg (79%); white solid; mp 173–174 °C.
1 H), 7.65 (dd, J = 1.2, 8.4 Hz, 1 H), 7.77 (dd, J = 1.6, 7.6 Hz, 1 H),
7.84 (d, J = 1.2 Hz, 1 H), 7.99 (d, J = 8.4 Hz, 1 H), 8.04 (d,
J = 8.4 Hz, 2 H), 8.16 (d, J = 8.4 Hz, 1 H).
13C NMR (100 MHz, CDCl3): d = 21.4, 121.9, 123.7, 126.5, 127.5,
128.4, 129.0, 129.9, 130.9, 133.7, 134.9, 138.5, 140.3, 140.7, 149.6,
159.0, 169.2.
IR (film): 3057, 2921, 1906, 1642, 1608, 1559, 1537, 1484, 1450,
1376, 1334, 1308, 988, 759, 733 cm–1.
1H NMR (400 MHz, CDCl3): d = 2.36 (s, 3 H), 2.48 (s, 3 H), 7.15
(d, J = 8.0 Hz, 2 H), 7.31 (d, J = 8.0 Hz, 2 H), 7.51–7.55 (m, 1 H),
7.56 (d, J = 8.4 Hz, 2 H), 7.80–7.84 (m, 1 H), 7.98 (d, J = 8.4 Hz,
1 H), 8.12 (d, J = 8.4 Hz, 2 H), 8.15 (d, J = 8.4 Hz, 1 H).
HRMS (ESI): m/z [M + H]+ calcd for C21H16ClN2S: 363.0723;
found: 363.0724.
13C NMR (100 MHz, CDCl3): d = 21.4, 121.9, 123.7, 124.2, 126.5,
128.4, 128.9, 129.1, 129.9, 133.6, 135.1, 136.0, 139.6, 140.6, 149.4,
159.0, 171.1.
4-Benzylsulfanyl-2-p-tolylquinazoline (7m)
Yield: 26.4 mg (77%); white solid; mp 136–137 °C.
IR (KBr): 1815, 1608, 1539, 1450, 1376, 1316, 1249, 1000, 868,
760, 700 cm–1.
1H NMR (400 MHz, CDCl3): d = 2.44 (s, 3 H), 4.78 (s, 2 H), 7.26–
7.34 (m, 5 H), 7.47–7.51 (m, 3 H), 7.79 (s 1 H), 7.97 (d, J = 8.4 Hz,
1 H), 8.01 (d, J = 8.4 Hz, 1 H), 8.51 (d, J = 8.4 Hz, 2 H).
HRMS (ESI): m/z [M + H]+ calcd for C22H19N2S: 343.1269; found:
343.1271.
4-Phenylsulfanyl-2-p-tolylquinazoline (7i)
Yield: 26.6 mg (81%); white solid; mp 147–148 °C.
IR (Br): 3060, 2918, 1609, 1559, 1539, 1485, 1450, 1337, 1308,
13C NMR (100 MHz, CDCl3): d = 21.5, 33.8, 122.2, 123.7, 126.4,
127.4, 128.5, 128.7, 128.9, 129.2, 129.3, 133.6, 135.7, 137.3, 140.8,
149.1, 158.9, 170.3.
HRMS (ESI): m/z [M + H]+ calcd for C22H19N2S: 343.1269; found:
343.1274.
1177, 756, 687 cm–1
.
1H NMR (400 MHz, CDCl3): d = 2.36 (s, 3 H), 7.15 (d, J = 8.0 Hz,
2 H), 7.51–7.57 (m, 4 H), 7.69–7.71 (m, 2 H), 7.81–7.85 (m, 1 H),
7.98 (d, J = 8.4 Hz, 1 H), 8.09 (d, J = 8.0 Hz, 2 H), 8.16–8.18 (m,
1 H).
2-(4-Chlorophenyl)-4-p-tolylsulfanylquinazoline (7n)
Yield: 28.7 mg (79%); white solid; mp 136–137 °C.
13C NMR (100 MHz, CDCl3): d = 21.4, 121.8, 123.7, 126.5, 127.7,
128.4, 129.0, 129.1, 129.4, 133.7, 135.0, 136.2, 140.6, 149.5, 159.0,
170.8.
HRMS (ESI): m/z [M + H]+ calcd for C21H17N2S: 329.1112; found:
329.1115.
IR (KBr): 3032, 2921, 1957, 1919, 1893, 1816, 1784, 1614, 1593,
1577, 1493, 1451, 1376, 1335, 1252, 1088, 998, 756, 692 cm–1.
1H NMR (400 MHz, CDCl3): d = 2.49 (s, 3 H), 7.31–7.35 (m, 4 H),
7.54–7.58 (m, 3 H), 7.85 (t, J = 8.4 Hz, 1 H), 7.97 (d, J = 8.4 Hz,
1 H), 8.15–8.19 (m, 3 H).
4-(4-Fluorophenylsulfanyl)-2-p-tolylquinazoline (7j)
Yield: 29.5 mg (85%); white solid; mp 196–197 °C.
13C NMR (100 MHz, CDCl3): d = 21.5, 121.9, 123.7, 123.9, 127.2,
128.5, 128.6, 129.0, 129.7, 129.9, 133.8, 136.1, 136.3, 136.6, 139.8,
149.2, 158.0, 171.5.
IR (KBr): 3053, 2917, 2855, 1887, 1818, 1631, 1591, 1451, 1380,
732, 691 cm–1.
1H NMR (400 MHz, CDCl3): d = 2.37 (s, 3 H), 7.17–7.24 (m, 4 H),
7.54 (d, J = 7.2 Hz, 1 H), 7.65 (dd, J = 6.4, 7.2 Hz, 2 H), 7.82 (d,
J = 7.2 Hz, 1 H), 7.98 (d, J = 8.4 Hz, 1 H), 8.09–8.13 (m, 3 H).
HRMS (ESI): m/z [M + H]+ calcd for C21H16ClN2S: 363.0723;
found: 363.0725.
2-(4-Chlorophenyl)-4-phenylsulfanylquinazoline (7o)
Yield: 25.1 mg (72%); white solid; mp 214–215 °C.
13C NMR (100 MHz, CDCl3): d = 21.4, 116.2 (d, J = 22 Hz), 121.7,
122.9, 123.6, 126.7, 128.4, 129.0, 129.1, 133.8, 134.4, 138.3, 140.8,
149.4, 159.0, 162.5 (d, J = 248 Hz), 170.5.
HRMS (ESI): m/z [M + H]+ calcd for C21H16FN2S: 347.1018; found:
347.1012.
IR (KBr): 3048, 1921, 1816, 1614, 1592, 1560, 1482, 1450, 1382,
1335, 1089, 843, 756, 693 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.31 (d, J = 8.8 Hz, 2 H), 7.53–
7.59 (m, 4 H), 7.68–7.70 (m, 2 H), 7.86 (d, J = 1.2 Hz, 1 H), 7.99
(d, J = 8.4 Hz, 1 H), 8.15–8.19 (m, 3 H).
4-(4-Chlorophenylsulfanyl)-2-p-tolylquinazoline (7k)
Yield: 29.0 mg (80%); white solid; mp 206–208 °C.
13C NMR (100 MHz, CDCl3): d = 121.9, 123.7, 127.0, 127.5, 128.5,
129.0, 129.2, 129.6, 129.7, 133.9, 136.2, 136.3, 136.6, 140.3, 157.9,
171.3.
IR (KBr): 3050, 2917, 1898, 1818, 1607, 1576, 1557, 1542, 1478,
1451, 1377, 1324, 1094, 818, 732 cm–1.
1H NMR (400 MHz, CDCl3): d = 2.37 (s, 3 H), 7.18 (d, J = 8.0 Hz,
2 H), 7.48–7.56 (m, 3 H), 7.61 (d, J = 8.4 Hz, 2 H), 7.83 (s, 1 H),
7.98 (d, J = 8.4 Hz, 1 H), 8.10–8.12 (m, 3 H).
HRMS (ESI): m/z [M + H]+ calcd for C20H14ClN2S: 349.0566;
found: 349.0574.
2-(4-Chlorophenyl)-4-(4-fluorophenylsulfanyl)quinazoline (7p)
Yield: 31.2 mg (85%); white solid; mp 247–248 °C.
13C NMR (100 MHz, CDCl3): d = 21.4, 121.7, 123.5, 126.3, 126.9,
128.4, 129.0, 129.2, 129.9, 133.8, 134.8, 135.9, 137.4, 140.8, 149.5,
159.0, 170.1.
HRMS (ESI): m/z [M + H]+ calcd for C21H16ClN2S: 363.0723;
found: 363.0732.
IR (KBr): 3056, 2924, 1960, 1922, 1885, 1615, 1592, 1558, 1489,
1451, 1334, 1232, 1089, 1012, 842, 756, 692 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.22–7.26 (m, 2 H), 7.34 (d,
J = 8.4 Hz, 2 H), 7.60–7.68 (m, 3 H), 7.87 (t, J = 8.4 Hz, 1 H), 8.01
(d, J = 8.4 Hz, 1 H), 8.14–8.18 (m, 3 H).
4-(2-Chlorophenylsulfanyl)-2-p-tolylquinazoline (7l)
Yield: 27.9 mg (77%); white solid; mp 159–161 °C.
13C NMR (100 MHz, CDCl3): d = 116.5 (d, J = 24 Hz), 121.8,
123.6, 127.1, 128.5, 128.7, 129.0, 129.7, 134.1, 136.0, 136.8, 138.3,
138.4, 149.2, 157.9, 162.9 (d, J = 248 Hz), 171.5.
IR (KBr): 3057, 2917, 1925, 1810, 1608, 1558, 1541, 1482, 1456,
1379, 1335, 987, 753 cm–1.
1H NMR (400 MHz, CDCl3): d = 2.36 (s, 3 H), 7.14 (d, J = 8.0 Hz,
2 H), 7.39–7.41 (m, 1 H), 7.50 (d, J = 1.6 Hz, 1 H), 7.56–7.58 (m,
HRMS (ESI): m/z [M + H]+ calcd for C20H13ClFN2S: 367.0472;
found: 367.0474.
Synthesis 2012, 44, 1237–1246
© Thieme Stuttgart · New York