A. Kumar, R.A. Maurya / Tetrahedron 64 (2008) 3477e3482
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129.9, 144.0, 148.6, 148.7, 169.6. Analysis calculated for
C20H19NO2: C, 78.66; H, 6.27; N, 4.59. Found: C, 78.60; H,
6.22; N, 4.48.
(MþH). IR (neat, cmꢀ1): 2938, 1690, 1566, 1385, 1231. H
NMR (CDCl3, 300 MHz) d: 1.58 (s, 3H, CH3), 2.09 (s, 3H,
CH3), 2.19 and 2.25 (2s, 4la and 4lb, 3H, CH3), 2.36 (s, 3H,
CH3), 3.60 and 3.61 (2s, 4la and 4lb, 3H, OCH3), 4.52 and
4.61 (2s, 4la and 4lb, 1H, CH), 5.78 and 5.87 (2d,
J¼1.0 Hz, 4la and 4lb, 1H, CH), 7.00e7.57 (m, 8H, ArH).
13C NMR (CDCl3, 75 MHz) d: 12.8, 12.9, 16.1, 16.3, 17.2,
17.3, 19.1, 19.2, 44.3, 44.5, 49.2, 97.3, 97.4, 98.7, 113.6,
114.2, 123.3, 123.9, 124.7, 124.8, 124.9, 125.1, 125.2,
125.3, 126.5, 126.7, 126.8, 127.4, 128.1, 128.2, 128.3,
133.8, 133.9, 134.0, 137.1, 137.5, 137.6, 141.1, 141.5,
145.6, 145.9, 146.9, 147.0, 148.5, 168.1, 168.2. Analysis cal-
culated for C23H25NO2: C, 79.51; H, 7.25; N, 4.03. Found: C,
79.42; H, 7.16; N, 3.97.
4.3.8. 1-(4-Methoxy-phenyl)-2,5-dimethyl-4-phenyl-1,4-
dihydro-pyridine-3-carboxylic acid methyl ester (4h)
MS (ESI) m/z¼350 (MþH). IR (neat, cmꢀ1): 2947, 1690,
1
1567, 1508, 1439. H NMR (CDCl3, 300 MHz) d: 1.59 (s,
3H, CH3), 2.18 (s, 3H, CH3), 3.61 (s, 3H, OCH3), 3.84 (s,
3H, OCH3), 4.51 (s, 1H, CH), 6.00 (d, J¼1.3 Hz, 1H, CH),
6.94e6.99 (m, 2H, ArH), 7.13e7.42 (m, 7H, ArH). 13C
NMR (CDCl3, 75 MHz) d: 12.8, 12.9, 44.0, 48.8, 54.2, 98.6,
113.4, 114.1, 124.4, 124.5, 124.9, 126.4, 126.6, 126.7,
126.8, 127.5, 127.6, 127.7, 135.4, 145.6, 146.8, 157.3,
168.0. Analysis calculated for C22H23NO3: C, 75.62; H,
6.63; N, 4.01. Found: C, 76.54; H, 6.57; N, 3.98.
4.3.13. 2-Methyl-1,4-diphenyl-1,4-dihydro-pyridine-3-
carboxylic acid tert-butyl ester (4m)28
MS (ESI) m/z¼348 (MþH). IR (neat, cmꢀ1): 2956, 1690,
1571, 1235. 1H NMR (200 MHz, CDCl3) d: 1.34 (s, 9H,
3CH3), 2.16 (s, 3H, CH3), 4.71 (d, 1H, J¼5.1 Hz, CH), 5.00
(dd, 1H, J¼5.1 and 7.7 Hz, CH), 6.16 (d, 1H, J¼7.7 Hz,
CH), 7.22e7.47 (m, 10H, ArH). 13C NMR (50 MHz,
CDCl3) d: 19.1, 28.6, 41.3, 79.6, 103.7, 107.6, 126.5, 127.6,
128.0, 128.7, 129.7, 129.9, 144.2, 147.2, 149.2, 168.0. Analy-
sis calculated for C23H25NO2: C, 79.51; H, 7.25; N, 4.03.
Found: C, 79.40; H, 7.12; N, 3.90.
4.3.9. 2,5-Dimethyl-1,4-diphenyl-1,4-dihydro-pyridine-3-
carboxylic acid methyl ester (4i)
MS (ESI): m/z¼320 (MþH). IR (neat, cmꢀ1): 2945, 1690,
1
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1567, 1493, 1382, 1226. H NMR (CDCl3, 300 MHz) d: H
NMR (CDCl3, 200 MHz) d: 1.48 (s, 3H, CH3), 2.06 (s, 3H,
CH3), 3.50 (s, 3H, OCH3), 4.39 (s, 1H, CH), 5.96 (d,
J¼1.3 Hz, 1H, CH), 7.09e7.37 (m, 10H, ArH). 13C NMR
(CDCl3, 50 MHz) d: 17.3, 17.4, 44.5, 50.5, 99.7, 114.7,
124.4, 125.1, 126.1, 126.5, 126.7, 127.1, 128.5, 142.7,
145.6, 146.5, 168.2. Analysis calculated for C21H21NO2: C,
78.97; H, 6.63; N, 4.39. Found: C, 78.82; H, 6.58; N, 4.31.
4.3.14. 1-(4-Chlorophenyl)-2-methyl-4-phenyl-1,4-dihydro-
pyridine-3-carboxylic acid tert-butyl ester (4n)28
4.3.10. 4-(4-Methoxy-phenyl)-2-methyl-1-phenyl-1,4-
dihydro-pyridine-3-carboxylic acid methyl ester (4j)
MS (ESI) m/z¼382 (MþH). IR (neat, cmꢀ1): 2966, 1691,
1570, 1236. 1H NMR (200 MHz, CDCl3) d: 1.33 (s, 9H,
3CH3), 2.14 (s, 3H, CH3), 4.69 (d, 1H, J¼5.1 Hz, CH), 4.99
(dd, 1H, J¼5.1 and 7.7 Hz, CH), 6.10 (d, 1H, J¼7.7 Hz,
CH), 7.14e7.41 (m, 9H, ArH). 13C NMR (50 MHz, CDCl3)
d: 19.1, 28.6, 41.3, 79.7, 104.5, 108.0, 126.6, 127.9, 128.8,
129.2, 129.3, 130.1, 133.2, 142.8, 146.5, 148.9, 168.6. Analy-
sis calculated for C23H24ClNO2: C, 72.34; H, 6.33; N, 3.67.
Found: C, 72.41; H, 6.23; N, 3.51.
MS (ESI) m/z¼336 (MþH). IR (neat, cmꢀ1): 2946, 1692,
1595, 1236. 1H NMR (CDCl3, 200 MHz) d: 2.15 (s, 3H,
CH3), 3.45 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 4.96e5.05
(m, 2H, CH), 5.91 (d, J¼7.4 Hz, 1H, CH), 6.77e6.86 (m,
2H, ArH), 7.07e7.31(m, 7H, ArH). 13C NMR (CDCl3,
50 MHz) d: 19.0, 33.9, 51.0, 55.7, 107.6, 110.7, 121.2,
121.4, 127.2, 127.5, 128.0, 128.3, 129.5, 129.8, 156.0,
168.0. Analysis calculated for C21H21NO3: C, 75.20; H,
6.31; N, 4.18. Found: C, 75.02; H, 6.18; N, 4.11.
Acknowledgements
4.3.11. 1-(3-Chloro-phenyl)-2,5-dimethyl-4-phenyl-1,4-
dihydro-pyridine-3-carboxylic acid methyl ester (4k)
MS (ESI) m/z¼354 (MþH). IR (neat, cmꢀ1): 2943, 1694,
R.A.M. is thankful to CSIR, New Delhi for the award of
a SRF. Authors also acknowledge SAIF-CDRI for providing
spectral and analytical data.
1
1577, 1478, 1227. H NMR (CDCl3, 200 MHz) d: 1.56 (s,
3H, CH3), 2.15 (s, 3H, CH3), 3.59 (s, 3H, OCH3), 4.46 (s,
1H, CH), 6.03 (d, J¼1.3 Hz, 1H, CH), 7.08e7.37 (m, 9H,
ArH). 13C NMR (CDCl3, 50 MHz) d: 18.7, 18.9, 45.9, 51.1,
102.3, 116.6, 125.4, 126.1, 126.7, 127.8, 128.1, 128.6,
130.8, 135.4, 145.3, 146.7, 147.1, 169.4. Analysis calculated
for C21H20ClNO2: C, 71.28; H, 5.70; N, 3.96. Found: C,
71.12; H, 5.60; N, 3.87.
References and notes
1. Ramon, D. J.; Miguel, Y. Angew. Chem., Int. Ed. 2005, 44, 1602.
2. Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471.
3. Ugi, I.; Heck, S. Comb. Chem. High Throughput Screening 2001, 4, 1.
4. Weber, L.; IIIgen, K.; Almstetter, M. Synlett 1999, 366.
5. Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.; Dimarco, J. D.;
Gougoutas, J.; Hedberg, A.; Malley, M.; MaCarthy, J. P.; Zhang, R.;
Mereland, S. J. Med. Chem. 1995, 38, 119.
4.3.12. 1-(2,3-Dimethyl-phenyl)-2,5-dimethyl-4-phenyl-1,4-
dihydro-pyridine-3-carboxylic acid methyl ester (4l)
6. Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53,
2803.
The compound was isolated as 1.13:1 rotamer mixture (4la
major rotamer, 4lb minor rotamer). MS (ESI) m/z¼348
7. Aouam, K.; Berdeaux, A. Therapie 2003, 58, 333.
8. Hilgeroth, A. Mini-Rev. Med. Chem. 2002, 2, 235.