PAPER
Synthesis of Functionalized Fused Pyridines
1869
13C NMR (125 MHz, DMSO-d6): d = 29.1, 111.0, 117.3, 120.0,
124.9, 128.3, 130.8, 134.2, 137.9, 151.0, 154.5, 155.1, 156.8, 161.4,
193.9.
32
IR (KBr): 3600–3250 (br, OH), 3050, 2985, 2939, 1718 (ester
C=O), 1626 (C=O), 1603, 1579, 1444, 1306, 1240, 1142, 1072, 766,
750 cm–1.
9c
13C NMR (125 MHz, DMSO-d6): d = 12.9, 14.1, 61.7, 117.0, 119.5,
124.0, 127.1, 130.3, 131.0, 132.7, 134.3, 139.9, 150.2, 157.3, 162.1,
162.9, 195.3.
IR (KBr): 3600–3250 (br, OH), 3045, 2956, 2927, 1714, 1662, 1623
(C=O), 1600, 1497, 1454, 1329, 1288, 1153, 769 cm1.
13C NMR (125 MHz, DMSO-d6): d = 28.7, 30.0, 110.2, 117.3,
120.0, 124.8, 128.5, 130.9, 134.3, 138.3, 151.3, 153.1, 155.1, 156.9,
161.0, 193.9.
Quinolines 34, 36, 38, 40 from 3-Formylchromone (1) and
Anilines 33, 35, 37, 39; General Procedure
Aniline 33, 35, 37 or 39a–j (4.4 mmol) and 3-formylchromone 1
(696 mg, 4 mmol) were placed in a 25 mL ace pressure tube and dis-
solved in DMF (10 mL). Chlorotrimethylsilane (1.738 g, 16 mmol)
was added dropwise to the solution. The tube was thoroughly sealed
and heated on a water-bath for 12 h. After cooling, the flask was
opened (caution! excessive pressure inside), the mixture was
poured into H2O (30 mL) and allowed to stand at r.t. in an ultrasonic
bath for 1 h. The precipitate formed was filtered and washed with
MeOH (3 mL). Recrystallization from an appropriate solvent yield-
ed targeted compounds 34, 36, 38, 40a–j (Table 3).
9d
IR (KBr): 3600–3200 (br, OH), 3062, 3034, 2962, 2926, 1713,
1668, 1624 (C=O), 1608, 1593, 1497, 1340, 1242, 764 cm–1.
13C NMR (125 MHz, DMSO-d6): d = 28.8, 45.8, 110.4, 117.3,
120.0, 124.9, 127.6, 127.8, 128.8, 128.9, 130.9, 134.3, 137.3, 138.5,
151.3, 152.8, 155.1, 156.8, 161.0, 193.9.
10
IR (KBr): 3600–3275 (br, OH, NH), 3176, 3074, 3010, 2895, 2821,
1687 (uracyl C=O), 1624 (C = O), 1599, 1566, 1483, 1342, 1294,
1252, 1219, 1153, 987, 897, 814, 758, 646 cm–1.
34
IR (KBr): 3600–3300 (br, OH), 3070, 3051, 1624 (C=O), 1601,
1581, 1483, 1387, 1336, 1298, 1244, 1217, 957, 831, 818, 756, 719
cm–1.
13C NMR (125 MHz, DMSO-d6): d = 13.6, 114.7, 117.3, 120.0,
124.9, 130.3, 130.9, 134.3, 137.6, 156.0, 156.9, 160.3, 161.9, 164.1,
194.4.
13C NMR (125 MHz, DMSO-d6): d = 117.1, 119.6, 123.4, 123.9,
124.1, 127.3, 128.1, 128.1, 128.9, 129.5, 130.9, 131.3, 131.4, 132.1,
133.3, 134.4, 149.2, 149.6, 157.6, 195.9.
29a
IR (KBr): 3600–3300 (br, OH), 3086, 2972, 2926, 1623 (C=O),
1603, 1587, 1485, 1446, 1290, 1252, 1221, 976, 901, 764 cm–1.
36
13C NMR (125 MHz, DMSO-d6): d = 10.5, 113.31, 117.0, 119.5,
124.2, 130.4, 130.9, 134.2, 134.5, 152.5, 157.0, 157.4, 170.0, 194.4.
IR (KBr): 3600–3300 (br, OH), 3070, 3012, 2927, 1630 (C=O),
1605, 1579, 1477, 1419, 1294, 1246, 1165, 974, 856, 771, 712 cm–1.
13C NMR (125 MHz, DMSO-d6): d = 56.8, 57.3, 97.0, 100.7, 115.9,
117.4, 120.0, 124.8, 127.9, 131.1, 134.4, 136.5, 148.5, 153.6, 157.0,
157.6, 165.9, 193.7.
29b
IR (KBr): 3600–3200 (br, OH), 3059, 2978, 2931, 1630 (C=O),
1601, 1483, 1448, 1356, 1304, 1244, 1159, 764 cm–1.
13C NMR (125 MHz, DMSO-d6): d = 21.0, 27.1, 112.3, 117.5,
120.0, 124.5, 130.8, 131.5, 134.8, 134.9, 152.8, 157.6, 165.2, 170.7,
194.8.
38
IR (KBr): 3600–3300 (br, OH), 3068, 2997, 2949, 1635 (C=O),
1603, 1487, 1452, 1417, 1381, 1290, 1248, 1155, 1111, 1045, 931,
892, 818, 764 cm–1.
13C NMR (125 MHz, DMSO-d6): d = 57.3, 61.7, 62.5, 100.8, 117.5,
118.8, 120.0, 124.6, 128.7, 131.3, 134.6, 136.0, 141.9, 142.8, 147.1,
148.1, 157.4, 160.3, 193.9.
29c
IR (KBr): 3600–3300 (br, OH), 3172, 3059, 3032, 2960, 1622
(C=O), 1599, 1489, 1441, 1390, 1346, 1308, 1244, 1157, 903, 885,
744, 690, 644 cm–1.
13C NMR (125 MHz, DMSO-d6): d = 111.7, 117.5, 120.1, 124.2,
127.7, 128.3, 130.1, 131.7, 131.8, 131.9, 135.1, 135.2, 153.0, 157.8,
158.4, 171.1, 194.7.
40a
IR (KBr): 3600–3330 (br, OH), 3059, 2976, 2845, 1620 (C=O),
1605, 1524, 1460, 1363, 1271, 1236, 1163, 997, 920, 876, 773, 638
cm–1.
13C NMR (125 MHz, DMSO-d6): d = 56.7, 104.9, 108.6, 117.5,
120.0, 123.7, 124.6, 128.4, 131.1, 134.5, 139.9, 142.0, 142.8, 151.8,
157.0, 157.2, 193.4.
30
IR (KBr): 3600–3330 (br, OH), 3064, 3028, 2981, 2958, 2924, 1626
(C=O), 1589, 1479, 1446, 1352, 1302, 1246, 1209, 860, 777, 750
cm–1.
13C NMR (125 MHz, DMSO-d6): d = 18.3, 117.5, 120.0, 124.5,
127.5, 130.6, 131.6, 133.7, 134.9, 151.4, 157.8, 164.4, 174.3, 195.5.
40b
IR (KBr): 3600–3250 (br, OH), 3062, 3028, 2974, 2947, 1649
(C=O), 1624, 1605, 1506, 1462, 1354, 1281, 1246, 1157, 1005, 912,
756 cm–1.
13C NMR (125 MHz, DMSO-d6): d = 56.6, 56.8, 105.1, 107.9,
117.4, 119.9, 123.4, 124.9, 129.2, 131.1, 134.3, 139.5, 143.4, 145.5,
151.1, 155.9, 157.2, 194.9.
31
IR (KBr): 3600–3300 (br, OH), 3145, 3107, 3068, 2964, 1749 (ester
C=O), 1626 (C=O), 1595, 1572, 1437, 1381, 1213, 1161, 818, 762,
733, 652 cm–1.
13C NMR (125 MHz, DMSO-d6): d = 53.2, 114.5, 117.3, 119.2,
119.9, 124.9, 131.1, 131.4, 134.4, 135.3, 145.8, 149.5, 157.2, 159.1,
163.2, 195.4.
40c
IR (KBr): 3600–3250 (br, OH), 3057, 2983, 2926, 1637 (C=O),
1605, 1506, 1473, 1456, 1282, 1246, 1165, 1012, 914, 750 cm–1.
Synthesis 2007, No. 12, 1861–1871 © Thieme Stuttgart · New York