Substituted 3-Aminoindolizines
1245
Isopropyl 2-dimethoxymethyl-3-methoxycarbonyl-6-methyl-4-(2-nitrophenyl)-
1,4-dihydropyridine-5-carboxylate (4; C21H26N2O8)
1
Yield: 56%; m.p.: 145±147ꢁC (Ref. [14]: 143±145ꢁC); H NMR (CDCl3, ꢂ, 500 MHz): 7.75±7.26
(m, 4Har), 6.71 (s, NH), 5.96 (s, CH), 5.88 (s, H-4), 4.96 (m, OCH), 3.60 (s, OCH3), 3.38, 3.46 (s,
OCH3), 2.39 (s, CH3), 1.24, 0.98, (d, CH3, J 6.2 Hz) ppm; 13C NMR (CDCI3, ꢂ, 75 MHz): 166.7
(CO2CH3), 166.6 (CO), 147.7 (C20), 144.6 (C6), 143.7 (C2), 142.3 (C10), 133.0 (C40), 131.3 (C60),
127.2 (C50), 124.1 (C30), 105.0 (C3), 103.7 (C5), 98.5 (OCHO), 67.4 (OCH), 55.6, 55.1 (OCH3),
51.4 (OCH3), 34.8 (C4), 21.8, 21.4 19.6 (CH3) ppm; IR (KBr): ꢃ 3359 (N±H), 1697 (C=O) cmꢀ1
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Ethyl 2-dimethoxymethyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-
1,4-dihydropyridine-5-carboxylate (5; C20H24N2O8)
Yield: 63%; m.p.: 88±90ꢁC; 1H NMR (CDCl3, ꢂ, 500 MHz): 8.16±7.40 (m, 4Har), 6.96 (s, NH), 6.03
(s, CH), 5.17 (s, H-4), 4.10 (q, OCH2), 3.68 (s, OCH3), 3.49, 3.45 (s, OCH3), 2.40 (s, CH3), 1.24
(t, CH3) ppm; 13C NMR (CDCl3, ꢂ, 75 MHz): 166.7 (CO2CH3), 166.3 (CO), 149.1 (C10), 148.7 (C30),
144.8 (C6), 144.1 (C2), 134.0 (C60), 128.7 (C50), 122.6 (C20), 121.3 (C40), 104.0 (C3), 102.5 (C5),
98.4 (OCHO), 59.8 (OCH2), 55.4, 54.9 (OCH3), 51.2 (OCH3), 39.7 (C4), 19.3, 14.0 (CH3) ppm; IR
(KBr): ꢃ 3372 (N±H), 1682 (C=O) cmꢀ1
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Isopropyl 2-dimethyoxymethyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-
1,4-dihydropyridine-5-carboxylate (6; C21H26N2O8)
Yield: 49%; m.p.: 100±102ꢁC (Ref. [14]: oil); 1H NMR (CDCl3, ꢂ, 500 MHz): 8.14±7.39 (m, 4Har),
6.81 (s, NH), 6.02 (s, CH), 5.12 (s, H-4), 4.97 (m, OCH), 3.67 (s, OCH3), 3.49, 3.46 (s, OCH3), 2.38
(s, CH3), 1.26, 1.12 (d, CH3 J 6.2 Hz), ppm; 13C NMR (CDCl3, ꢂ, 75 MHz): 166.6 (CO2CH3),
166.4 (CO), 149.4 (C10), 148.2 (C30), 144.6 (C6), 144.2 (C2), 134.3 (C60), 128.8 (C50), 123.0 (C20),
121.5 (C40), 104.2 (C3), 103.2 (C5), 98.6 (OCHO), 67.4 (OCH), 55.7, 55.1 (OCH3), 51.5 (OCH3),
40.0 (C4), 22.1, 21.8, 19.6 (CH3) ppm; IR (KBr): ꢃ 3359 (N±H), 1697 (C=O) cmꢀ1
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Ethyl 2-dimethoxymethyl-3-methoxycarbonyl-6-methyl-4-(4-nitrophenyl)-
1,4-dihydropyridine-5-carboxylate (7; C20H24N2O8)
1
Yield: 55% ; yellow oil; H NMR (CDCl3, ꢂ, 500 MHz): 8.09 (d, 2Har), 7.52 (d, 2Har, J 8.8 Hz),
7.19 (s, NH), 6.04 (s, CH), 5.21 (s, H-4), 4.10 (q, OCH2), 3.68 (s, OCH3), 3.47, 3.42 (s, OCH3), 2.43
(s, CH3), 1.23 (t, CH3), ppm; 13C NMR (CDCl3, ꢂ, 75 MHz): 167.0 (CO2CH3), 166.7 (CO), 154.8
(C10), 146.7 (C40), 145.6 (C6), 144.5 (C2), 128.9 (C60, C20), 123.5 (C50, C30), 104.1 (C3), 102.5 (C5),
99.0 (OCHO), 60.0 (OCH2), 55.6, 55.4 (OCH3), 51.4 (OCH3), 40.4 (C4), 19.3, 14.4 (CH3) ppm; IR
(KBr): ꢃ 3393 (N±H), 1697 (C=O) cmꢀ1
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Isopropyl 2-dimethoxymethyl-3-methoxycarbonyl-6-methyl-4-(4-nitrophenyl)-
1,4-dihydropyridine-5-carboxylate (8; C21H26N2O8)
1
Yield: 57%; yellow oil; H NMR (CDCl3, ꢂ, 500 MHz): 8.09 (d, 2Har), 7.53 (d, 2Har, J 8.8 Hz),
7.15 (s, NH), 6.04 (s, CH), 5.19 (s, H-4), 4.98 (m, OCH), 3.68 (s, OCH3), 3.46, 3.42 (s, OCH3), 2.43
(s, CH3), 1.25, 1.13 (d, CH3, J 6.2 Hz) ppm; 13C NMR (CDCl3, ꢂ, 75 MHz): 166.7 (CO2CH3),
166.4 (CO), 154.9 (C10), 146.7 (C40), 145.3 (C6), 144.5 (C2), 129.0 (C60, C20), 123.4 (C50, C30), 104.1
(C3), 102.8 (C5), 99.0 (OCHO), 67.4 (OCH), 55.6, 55.3 (OCH3), 51.4 (OCH3), 40.4 (C4), 22.1, 21.9,
19.3 (CH3) ppm; IR (KBr): ꢃ 3383 (N±H), 1697 (C=O) cmꢀ1
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