HETEROCYCLES, Vol. 65, No. 1, 2005
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132.94, 145.20, 147.56, 157.02, 167.18. Anal. Calcd for C17H16N2O6: C, 59.30; H, 4.68; N, 8.14. Found: C,
59.1; H, 4.5; N, 8.0.
2,6-Dimethyl-3-methoxycarbonyl-4-(m-nitrophenyl)-5-ethoxycarbonylpyridine (21). Yellow oil; yield
0.69 g (96%). Rf (10% C2H5OAc/CH2Cl2) 0.36; IR ν (liquid film): 2983, 1721, 1560, 1438, 1373, 1293,
1214, 1108 cm-1. 1H-NMR (CDCl3) δ: 1.01 (3H, t, J = 7.1 Hz, CH3), 2.63 (3H, s, CH3), 2.64 (3H, s, CH3),
3.59 (3H, s, OCH3), 4.07 (2H, q, J = 14.3 Hz, CH2), 7.57–7.63 (2H, m, Ph), 8.17–8.18 (1H, m, Ph),
13
8.23–8.30 (1H, m, Ph). C-NMR (CDCl3) δ: 13.55, 22.94, 22.98, 52.25, 61.54, 123.03, 123.29, 129.12,
134.06, 137.90, 143.45, 147.70, 155.97, 156.09, 167.00, 167.55. MS (m/z, %) 359 (MH,+ 100), 341 (19),
327 (9), 313 (10). Anal. Calcd for C18H18N2O6: C, 60.33; H, 5.06; N, 7.82. Found: C, 60.2; H, 5.0; N, 7.7.
2,6-Dimethyl-3-isobutyloxycarbonyl-4-(o-nitrophenyl)-5-methoxycarbonylpyridine (22). Yellow oil;
yield 0.59 g (76%). Rf (10% C2H5OAc/CH2Cl2) 0.37; IR ν (liquid film): 2962, 1729, 1559, 1532, 1349,
1236, 1110, 1042 cm-1. 1H-NMR (CDCl3) δ: 0.67 (6H, d, J = 6.9 Hz, (CH3)2CH), 1.52–1.59 (1H, m, CH),
2.56 (3H, s, CH3), 2.58 (3H, s, CH3), 3.41 (3H, s, OCH3), 3.52–3.55 (1H, m, CH2CH), 3.69–3.72 (1H, m,
CH2CH), 7.13–7.15 (1H, m, Ph), 7.47–7.50 (1H, m, Ph), 7.54–7.57 (1H, m, Ph), 8.11–8.13 (1H, dd, J1 = 8.1
Hz, J2 = 1.2 Hz, Ph). 13C-NMR (CDCl3) δ: 18.71, 18.76, 23.42, 23.52, 27.27, 51.93, 71.56, 124.20, 124.49,
125.04, 129.36, 130.06, 131.87, 132.73, 144.62, 147.42, 156.56, 156.70, 166.82, 167.08. Anal. Calcd for
C20H22N2O6: C, 62.17; H, 5.74; N, 7.25. Found: C, 62.0; H, 5.6; N, 7.1.
2-[2-(N-Phthalimido)ethoxymethyl]-3-ethoxycarbonyl-4-(o-chlorophenyl)-5-methoxycarbonyl-6-
methylpyridine (23). Pale yellow plates; mp 121.0-123.0°C (from izopropyl ether); yield 1.04 g (97%). Rf
1
(10% C2H5OAc/CH2Cl2) 0.25; IR ν (KBr): 1772, 1717, 1563, 1392, 1231, 1114, 717 cm-1. H-NMR
(CDCl3) δ: 0.91 (3H, t, J = 7.1 Hz, CH2CH3), 2.61 (3H, s, CH3), 3.53 (3H, s, OCH3), 3.72 (2H, t, J = 5.8 Hz,
CH2), 3.88 (2H, t, J = 5.8 Hz, CH2), 4.01 (2H, q, J = 13.9 Hz, CH2), 4.82–4.90 (2H, m, CH2), 7.14 (1H, dt,
J1 = 7.3 Hz, J2 = 1.6 Hz, Ph), 7.23–7.33 (2H, m, Ph), 7.39 (1H, d, J = 7.4, Ph), 7.70 (2H, dd, J1 = 3.0 Hz, J2
= 5.4 Hz, Ph), 7.83 (2H, dd, J1 = 3.0 Hz, J2 = 5.4 Hz, Ph). 13C-NMR (CDCl3) δ: 13.45, 23.18, 37.33, 52.17,
61.36, 67.60, 72.84, 123.19, 126.05, 126.42, 128.20, 129.05, 129.77, 130.29, 132.17, 132.89, 133.83,
134.97, 144.93, 156.09, 166.29, 167.35, 168.13. MS (m/z, %) 537 (MH,+ 100), 407 (16), 347 (12), 345 (16),
268 (16), 260 (17), 174 (10). Anal. Calcd for C28H25N2O7Cl: C, 62.63; H, 4.69; N, 5.22; Cl, 6.60. Found: C,
62.5; H, 4.6; N, 5.1; Cl, 6.5.
2-(2-Aminoethoxy)methyl-3-ethoxycarbonyl-4-(o-chlorophenyl)-5-methoxycarbonyl-6-methyl-
pyridine as acetate salt (24). Pale yellow powder; mp 100.0-103.0°C (from isopropyl ether); yield 0.86 g
(92%). Rf (3% NH3(aq)/17% CH3OH/40% CH3CN/40% dioxane) 0.54; IR ν (KBr): 2988, 2952, 1727,
1555, 1434, 1415, 1236 cm-1. 1H-NMR (CDCl3) δ: 0.90 (3H, t, J = 7.1 Hz, CH2CH3), 1.92 (3H, s, CH3),
2.65 (3H, s, CH3CO), 3.08 (2H, t, J = 4.8 Hz, CH2), 3.54 (3H, s, OCH3), 3.72 (2H, t, J = 4.9 Hz, CH2), 4.00
(2H, q, J = 7.1 Hz, CH2CH3), 4.81 (1H, d, J = 13.4 Hz, CH2O), 4.84 (1H, d, J = 13.4 Hz, CH2O), 7.17 (1H,