ONE-POT SYNTHESIS OF 1,4-DIHYDROPYRIDINES
3255
Compound 4d. White crystals. IR (KBr) n: 3376, 1685, 1619, 1490, 1202 cmꢁ1
.
1H NMR (400 MHz, CDCl3) d (ppm): 7.26 (s, 1H, ArH), 7.12 (d, J ¼ 8.0 Hz, 1H,
ArH), 7.09 (d, J ¼ 8.0 Hz, 1H, ArH), 5.60 (brs, 1H, NH), 5.35 (s, 1H, CH), 4.08
(q, J ¼ 7.2 Hz, 4H, 2CH2O), 2.30 (s, 6H, 2CH3), 1.21 (t, J ¼ 7.2 Hz, 6H, 2CH3).
13C NMR (100 MHz, CDCl3) d (ppm): 167.4, 144.2, 144.0, 133.2, 132.5, 132.1,
128.9, 127.3, 103.6, 59.8, 37.3, 19.7, 14.3.
Compound 4e. Pale yellow crystals. IR (KBr) n: 3344, 1705, 1646, 1487,
1213 cmꢁ1 1H NMR (400 MHz, CDCl3) d (ppm): 8.00–8.09 (m, 2H, ArH),
.
7.34–7.51 (m, 2H, ArH), 5.76 (brs, 1H, NH), 5.12 (s, 1H, CH), 4.10 (q, J ¼ 7.2 Hz,
4H, 2CH2O), 2.36 (s, 6H, 2CH3), 1.22 (t, J ¼ 7.2 Hz, 6H, 2CH3). 13C NMR
(100 MHz, CDCl3) d (ppm): 167.5, 150.1, 148.3, 145.0, 134.5, 128.9, 123.1, 121.4,
104.1, 59.9, 38.1, 19.5, 14.1.
Compound 4f. Yellow solid. IR (KBr) n: 3324, 1698, 1646, 1487, 1217 cmꢁ1
.
1H NMR (400 MHz, CDCl3). d (ppm): 8.03 (d, J ¼ 8.8 Hz, 2H, ArH), 7.38 (d,
J ¼ 8.8 Hz, 2H, ArH), 5.69 (brs, 1H, NH), 5.03 (s, 1H, CH), 4.10 (q, J ¼ 7.2 Hz,
4H, 2CH2O), 2.25 (s, 6H, 2CH3), 1.20 (t, J ¼ 7.2 Hz, 6H, 2CH3). 13C NMR
(100 MHz, CDCl3) d (ppm): 167.4, 150.6, 146.3, 144.9, 126.3, 122.7, 103.6, 59.8,
38.9, 19.4, 14.2.
Compound 4g. Yellow crystals. IR (KBr) n: 3341, 1691, 1649, 1491,
1
1211 cmꢁ1. H NMR (400 MHz, CDCl3) d (ppm): 7.18 (d, J ¼ 8.0 Hz, 2H, ArH),
6.72 (d, J ¼ 8.0 Hz, 2H, ArH), 5.68 (brs, 1H, NH), 4.95 (s, 1H, CH), 4.10 (q,
J ¼ 7.2 Hz, 4H, 2CH2O), 3.77 (s, 3H, CH3O), 2.34 (s, 6H, 2CH3), 1.23 (t, J ¼ 7.2 Hz,
6H, 2CH3). 13C NMR (100 MHz, CDCl3) d (ppm): 167.4, 157.8, 146.3, 136.6, 131.3,
113.8, 103.6, 59.8, 53.7, 39.4, 19.4, 14.2.
Compound 4h. Yellow crystals. IR (KBr) n: 3319, 1689, 1651, 1489,
1200 cmꢁ1 1H NMR (400 MHz, CDCl3) d (ppm): 7.29–7.36 (m, 2H, ArH),
.
6.79–6.85 (m, 2H, ArH), 5.78 (brs, 1H, NH), 5.10 (s, 1H, CH), 4.10 (q, J ¼ 7.2 Hz,
4H, 2CH2O), 3.91 (s, 3H, CH3O), 2.33 (s, 6H, 2CH3), 1.25 (t, J ¼ 7.2 Hz, 6H,
2CH3). 13C NMR (100 MHz, CDCl3) d (ppm): 167.4, 158.5, 146.3, 131.5, 127.7,
122.3, 121.8, 112.8, 103.6, 59.8, 54.4, 32.6, 19.4, 14.2.
Compound 4i. Pale yellow crystals. IR (KBr) n: 3358, 1695, 1652, 1487,
1
1214 cmꢁ1. H NMR (400 MHz, CDCl3) d (ppm): 7.04–7.12 (m, 4H, ArH), 5.70
(brs, 1H, NH), 4.95 (s, 1H, CH), 4.09 (q, J ¼ 7.2 Hz, 4H, 2CH2O), 2.34 (s, 6H,
2CH3), 2.21 (s, 3H, CH3), 1.19 (t, J ¼ 7.2 Hz, 6H, 2CH3). 13C NMR (100 MHz,
CDCl3) d (ppm): 167.8, 146.4, 144.1, 135.5, 128. 4, 127.9, 103.9, 59.7, 39.3, 21.2,
19.5, 14.3.
Compound 4j. White solid. IR (KBr) n: 3346, 1660, 1634, 1488, 1231 cmꢁ1
.
1H NMR (400 MHz, CDCl3) d (ppm): 6.98 (d, J ¼ 8.4 Hz, 2H, ArH), 6.76 (d,
J ¼ 8.4 Hz, 2H, ArH), 5.52 (brs, 1H, NH), 5.29 (s, 1H, OH), 4.97 (s, 1H, CH),
4.09 (q, J ¼ 7.2 Hz, 4H, 2CH2O), 2.35 (s, 6H, 2CH3), 1.26 (t, J ¼ 7.2 Hz, 6H,
2CH3). 13C NMR (100 MHz, CDCl3) d (ppm): 167.8, 155.8, 146.4, 135.3, 131.7,
115.2, 103.9, 59.7, 39.3, 19.5, 14.3.