TABLE 2 (continued)
1
2
3
5i
1640, 1630;
3350, 3200,
3080
0.94 (3Н, s, СН3); 1.08 (3Н, s, СН3); 2.07 (1Н, d, 2J = 18, СН);
2.18 (1Н, d, 2J = 18, СН); 2.61 (2Н, s, СН2); 5.88 (1Н, d, 3J = 5, СН);
6.72 (1H, d, 3J = 8, C6H3); 7.18 (3H, m, С6H3, NH);
7.57 (6Н, m, C6H5, C6H4); 7.97-8.07 (3Н, m, C6H4);
9.08 (1H, br. s, NH)
5j
5k
5l
1645, 1630;
3320, 3180,
3070
0.99 (3Н, s, СН3); 1.02 (3Н, s, СН3); 2.03 (1Н, d, 2J = 16, СН);
2.15 (1Н, d, 2J = 16, СН); 2.53 (2Н, s, СН2); 5.71 (1Н, br. s, СН);
6.66 (1H, d, 3J = 8, C6H3); 7.07-7.56 (9Н, m, C5H4N, C6H4, NH);
8.31 (3Н, m, C6H4, C6H3); 8.98 (1H, br. s, NH)
1.01 (3Н, s, СН3); 1.03 (3Н, s, СН3); 2.06 (1Н, d, 2J = 17, СН);
2.18 (1Н, d, 2J = 17, СН); 2.53 (2Н, s, СН2); 5.96 (1Н, d, 3J = 2, СН);
6.74-7.08 (5Н, m, C6H3, C4H3S); 7.04 (1H, d, 3J = 5, NH);
7.59 (6Н, m, C6H5, C6H3); 8.99 (1H, br. s, NH)
0.93 (3Н, s, СН3); 1.03 (3Н, s, СН3); 2.11 (1Н, d, 2J = 17, СН);
2.26 (1Н, d, 2J = 17, СН); 2.53 (2Н, s, СН2); 5.77 (3Н, m, C4H3O);
6.14 (1Н, m, C6H3); 6.71 (1Н, d, 3J = 5, СН); 7.08 (2H, m, C6H3, NH);
7.36-7.69 (6Н, m, C6H5, C6H3); 8.98 (1H, br. s, NH)
1645, 1635;
3300, 3200,
3090
1640, 1630;
3320, 3200,
3100
5m
5n
5o
1630; 3350,
3220
0.93 (3Н, s, СН3); 1.08 (3Н, s, СН3); 2.04 (1Н, d, 2J = 18, СН);
2.17 (1Н, d, 2J = 18, СН); 2.61 (2Н, s, СН2); 5.71 (1Н, d, 3J = 5, СН);
6.58-7.27 (8Н, m, C6H4, C6H3, NH); 8.99 (1H, br. s, NH)
0.96 (3Н, s, СН3); 1.07 (3Н, s, СН3); 2.05 (1Н, d, 2J = 16, СН);
2.17 (1Н, d, 2J = 16, СН); 2.61 (2Н, s, СН2); 5.72 (1Н, d, 3J = 5, СН);
6.64-7.29 (8Н, m, C6H4, C6H3, NH); 9.04 (1H, d, 3J = 5, NH)
1632; 3320,
3200, 3090
1630, 3300,
3210, 3100
1.01 (3Н, s, СН3); 1.05 (3Н, s, СН3); 2.04 (1Н, d, 2J = 16, СН);
2.19 (1Н, d, 2J = 16, СН); 2.24 (2Н, s, СН2); 5.90 (1Н, d, 3J = 5, СН);
6.73-7.30 (7Н, m, C6H3, C4H3S, NH); 9.00 (1H, br. s, NH)
5p
1630;
3330, 3200,
3100-3050
0.96 (3Н, s, СН3); 1.08 (3Н, s, СН3); 2.04 (1Н, d, 2J = 16, СН);
2.16 (1Н, d, 2J = 16, СН); 2.53 (2Н, s, СН2);
5.73 (2Н, m, C4H3O, СН); 6.12 (1H, m, C4H3O);
6.71-7.38 (5Н, m, C6H3, C4H3O, NH); 8.93 (1H, br. s, NH)
5q
5r
1635;
3350, 3240,
3100-3050
1.01 (3Н, s, СН3); 1.06 (3Н, s, СН3); 2.05 (1Н, d, 2J = 18, СН);
2.18 (1Н, d, 2J = 18, СН); 2.52 (2Н, s, СН2); 5.99 (1Н, d, 3J = 6, СН);
6.79-7.58 (6Н, m, C6H3, C4H3S, NH); 7.97 (1H, d, 4J = 2, C6H3);
9.17 (1H, br. s, NH)
1631;
3330, 3200,
3100-3050
0.92 (3Н, s, СН3); 1.03 (3Н, s, СН3); 2.02 (1Н, d, 2J = 18, СН);
2.16 (1Н, d, 2J = 18, СН); 2.52 (2Н, s, СН2); 5.81 (2Н, m, C4H3N, СН);
6.12 (1H, m, C4H3O); 6.82 (1Н, d, 3J = 8, C6H3);
7.43-7.58 (2Н, m, C4H3O, NH); 7.62 (1Н, dd, 3J = 8, 4J = 2, C6H3);
7.97 (1Н, d, 4J = 2, C6H3); 9.12 (1H, br. s, NH)
5s
1630;
3300, 3210,
3100
1.05 (3Н, s, СН3); 1.12 (3Н, s, СН3); 2.23 (2Н, s, СН2);
2.52 (2Н, s, СН2); 3.67 (3Н, s, OCH3); 3.81 (3Н, s, OCH3);
4.96 (1H, br. s, NH); 5.72 (1H, br. s, СН); 6.62 (3H, m, C6H3);
7.18 (1H, s, C6H2); 7.43 (1H, s, C6H2); 8.43 (1H, br. s, NH)
5t
1632;
3340, 3200,
3100
1.12 (3Н, s, СН3); 1.15 (3Н, s, СН3); 2.25 (2Н, s, СН2);
2.61 (2Н, s, СН2); 5.87 (1Н, s, CH); 6.47-6.83 (4Н, m, C6H3, NH);
6.85 (1H, s, C6H2); 7.47 (1H, s, C6H2); 8.61 (1H, br. s, NH)
5u
1630;
3320, 3220,
3100
1.06 (3Н, s, СН3); 1.07 (3Н, s, СН3); 2.21 (2Н, s, СН2);
2.61 (2Н, s, СН2); 5.78 (1Н, d, 3J = 5, CH); 6.66 (1Н, d, 3J = 5, NH);
6.84 (1H, s, C6H2); 7.27 (1H, s, C6H2); 7.28-7.45 (2Н, m, C5H4N);
8.36 (2H, m, C5H4N); 9.06 (1H, br. s, NH)
11-(2-Pyridyl)- (5b), 11-(3-Pyridyl)- (5c), 11-(4-Pyridyl)- (5d), 7-Methoxycarbonyl-11-(3-pyridyl)-
(5g), 7-Methoxycarbonyl-11-(4-pyridyl)- (5h), 7-Benzoyl-11-(4-pyridyl)- (5j), 7,8-Dichloro-11-(4-pyridyl)-
(5u)
3,3-dimethyl-1,2,3,4,10,11-hexahydro-5H-dibenzo[b,e][1,4]diazepin-1-ones.
The
corresponding
enaminone 3 (3 mmol) and pyridine carbaldehyde (3 mmol) were boiled in ethanol (40 ml) in the presence of
conc. H2SO4 (0.15 ml) for 3 h. Ethanol (25-30 ml) was distilled off on a rotary evaporator, water (40 ml) was
added, and the mixture was neutralized with a concentrated aqueous solution of NaHCO3. The precipitate was
filtered out and recrystallized from 2-propanol.
953