632
V. SIDDAIAH ET AL.
Diethyl-4-(2-chloro-5-nitrophenyl)-2,6-dimethyl-1,4-
dihydropyridine-3,5-carboxylate (9n)
Mp: 198–202 ꢀC. FT-IR (KBr): 3347, 1703, 1652, 1526, 1480, 1196, 1124,
1
716 cmꢁ1. H NMR (400 MHz, CDCl3): d ¼ 1.19 (t, J ¼ 7.0 Hz, 6H), 2.34 (s, 6H),
4.05 (q, J ¼ 7.0 Hz, 4H), 5.4 (s, 1H), 5.9 (s, 1H), 7.4 (d, J ¼ 8.8 Hz), 7.9 (dd,
J ¼ 8.8, 2.8 Hz), 8.2 (d, J ¼ 2.8 Hz). 13C NMR (22.5 MHz, CDCl3): d ¼ 13.9, 18.6,
38.0, 59.3, 101.7, 126.4, 129.7, 138.8, 145.9, 146.4, 147.7, 166.9. LCMS: m=z ¼ 393
(M-H)ꢁ. Anal. calcd. for C19H21NO6Cl: C, 57.86; H, 5.32; N, 3.55; Cl, 8.88. Found:
C, 57.82; H, 5.38; N, 3.59; Cl, 8.88.
Ethyl-1,4,7,8-tetrahydro-2,7,7-trimethyl-4-(2,3-
methylenedioxyphenyl)-5(6H)-oxoquinolin-3-carboxylate (11e)
Mp: 265–267 ꢀC. FT-IR (KBr): 3340, 2957, 1695, 1644, 1609, 1488, 1379, 1217,
1
1027, 753 cmꢁ1. H NMR (400 MHz, CDCl3 þ DMSO-d6): d ¼ 0.95 (s, 3H), 1.07 (s,
3H), 1.208 (t, J ¼ 7.2 Hz, 3H), 2.15–2.33 (m, 4H), 2.35 (s, 3H), 4.02–4.07 (m, 2H),
5.11 (s, 1H), 5.84–5.95 (m, 3H), 6.58 (dd, J ¼ 7.6, 1.2 Hz, 1H), 6.66 (dd, J ¼ 7.6,
8.0 Hz, 1H), 6.80 (dd, J ¼ 8.0, 1.2 Hz, 1H).13C NMR (22.5 MHz, CDCl3 þ DMSO-
d6): d ¼ 14.0, 19.2, 26.5, 29.5, 32.2, 35.1, 50.2, 50.5, 59.5, 99.8, 103.8, 110.1, 113.1,
120.6, 122.6, 131.6, 144.2, 144.4, 146.8, 147.9, 166.9, 194.2. LCMS: m=z ¼ 382
(M-H)-. Anal. calcd. for C22H25NO5: C, 68.92; H, 6.52; N, 3.65; Cl, 8.08. Found:
C, 68.89; H, 6.55; N, 3.61.
Ethyl-1,4,7,8-tetrahydro-2,7,7-trimethyl-4-(5-chloro-2,
3-dimethoxylphenyl)-5(6H)-oxoquinolin-3-carboxylate (11u)
Mp: 248–250 ꢀC. IR (KBr): 3297, 2956, 1703, 1648, 1606, 1496, 1381, 1215,
1
1031, 765 cmꢁ1. H NMR (400 MHz, CDCl3 þ DMSO-d6): d ¼ 1.00 (s, 3H), 1.068
(s, 3H), 1.214 (t, J ¼ 7.2 Hz, 3H), 2.15–2.26 (m, 4H), 2.29 (s, 3H) 3.77 (s, 3H), 3.86
(s, 3H), 4.05 (q, J ¼ 7.2 Hz, 2H), 5.11 (s, 1H), 6.0 (s, 1H), 6.5 (d, J ¼ 2.4, 1H), 6.9
(d, J ¼ 2.4, 1H). 13C NMR (22.5 MHz, CDCl3 þ DMSO-d6): d ¼ 14.5, 19.2, 26.7,
29.5, 32.1, 35.1, 49.2, 49.8, 55.2, 55.3, 59.5, 102.8, 110.1, 120.6, 126.6, 128.6, 134.6,
144.7, 145.4, 147.8, 149.9, 166.9, 194.3. LCMS: m=z ¼ 432 (M-H)-. Anal. Calcd.
for C23H28NO5Cl: C, 63.74; H, 6.46; N, 3.23; Cl, 8.08. Found: C, 63.71; H, 6.50;
N, 3.19; Cl, 8.03.
ACKNOWLEDGMENT
We gratefully acknowledge the financial support from the Department of
Science and Technology (DST), New Delhi.
REFERENCES
1. Clark, J.; Macquarrie, D. M. A. Handbook of Green Chemistry; Blackwell: Oxford, 2002.
2. Tanaka, K. Solvent-Free Organic Synthesis; Wiley-VCH: New York, 2003.