J. Chil. Chem. Soc., 60, Nº 1 (2015)
Ethyl2,6-bis(4-methoxyphenyl)-1-phenyl-4-(phenylamino)
tetrahydropyridine-3-carboxylate(4c):
2.34 (d, 2H, CH2), 3.69 (s, 6H, -OCH3), 4.14 (t, 1H, CH), 4.54 (s, 1H, CH),
4.05(s, 1H, NH), 6.49–6.67 (m, 4H, HAr), 6.34–6.49 (m, 4H, HAr),7.20-7.38
(m, 4H, HAr), 7.34-7.40 (m, 4H, HAr); IR (KBr, ν/cm–1): 3291, 1742, 2245,
1153, 1263, 1576; LC-MS (m/z): 584.21 (M+).
1H NMR (300 MHz, CDCl3) δ: 1.24 (t, 3 H, CH3), 4.08 (q, 2H, O-CH2),
2.31 (d, 2H, CH2), 3.63 (s, 6H, OCH3), 4.02 (s, 1H, NH), 4.09 (t, 1H, CH), 4.67
(s, 1H, CH), 6.59–6.98 (m, 5H, HAr), 6.37–6.91 (m, 5H, HAr),6.65–7.03 (m,
4H, HAr), 6.66–7.08 (m, 4H, HAr); IR (KBr, ν/cm–1): 3251, 1741, 1520, 1185,
1223; LC-MS (m/z): 536.21 (M+).
methyl-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydro-1-(4-
methoxyphenyl)-2,6-diphenylpyridine-3-carboxylate(4n):
1H NMR (300 MHz, CDCl3) δ: 3.79 (s, 3H, -O-CH3), 2.26 (d, 2H, CH2),
3.71 (s, 6H, -OCH ), 4.18 (t, 1H, CH), 4.61 (s, 1H, CH), 4.0 (s, 1H, NH),
6.44–6.64 (m, 4H, 3HAr), 6.37–6.53 (m, 4H, HAr), 7.03-7.11 (m, 5H, HAr),
7.09-7.16 (m, 5H, HAr); IR (KBr, ν/cm–1): 3259, 1732, 1143, 1276, 1519;
LC-MS (m/z): 520.16 (M+).
Ethyl2,6-bis(3,4,5-trimethoxyphenyl)-1-phenyl-4-(phenylamino)
tetrahydropyridine-3-carboxylate(4d):
1H NMR (300 MHz, CDCl ) δ: 1.22 (t, 3H, CH ), 4.06 (q, 2H, O-CH2),
2.29 (d, 2H, CH ), 3.7 (s, 18H, 3OCH ), 4.03 (s, 1H,3NH), 4.01 (t, 1H, CH),
4.7 (s, 1H, CH), 26.6–7.08 (m, 5H, HA3r), 6.41–7.01 (m, 5H, HAr),6.03 (s, 2H,
HAr), 6.03 (s, 2H, HAr); IR (KBr, ν/cm–1): 3243, 1737, 1521, 1156, 1243;
LC-MS (m/z): 656.41 (M+).
Ethyl-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydro-1-(4-
methoxyphenyl)-2,6-dip-tolylpyridine-3 carboxylate(4o):
1H NMR (300 MHz, CDCl3) δ: 1.26 (t, 3H, CH3), 4.11 (q, 2H, -O-CH2),
2.28 (d, 2H, CH ), 2.31 (s, 6H, CH ), 3.73 (s, 6H, -OCH ), 4.13 (t, 1H, CH),
4.57 (s, 1H, CH2), 3.96 (s, 1H, NH3), 6.46–6.60 (m, 4H, 3HAr), 6.91 (m, 4H,
HAr), 7.03 (m, 4H, HAr), 7.04 (m, 4H, HAr); IR (KBr, ν/cm–1): 3263, 1734,
1145, 1266, 1519; LC-MS (m/z): 562.23 (M+).
Ethyl2,6-bis(2-methoxyphenyl)-1-phenyl-4-(phenylamino)
tetrahydropyridine-3-carboxylate(4e):
1H NMR (300 MHz, CDCl3) δ: 3.52 (s, 3H, CH3), 2.33 (d, 2H, CH2), 3.68
(s, 6H, OCH ), 4.01 (s, 1H, NH), 3.87 (t, 1H, CH), 4.67 (s, 1H, CH), 6.51–7.11
(m, 5H, HAr3), 6.43–7.04 (m, 5H, HAr), 6.73 - 6.97 (s, 4H, HAr), 6.67- 6.97 (s,
4H, HAr); IR (KBr, ν/cm–1): 3307, 1743, 1540, 1152, 1210; LC-MS (m/z):
522.11 (M+).
Ethyl-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydro-1,2,6-tris(4-
methoxyphenyl)pyridine-3-carboxylate(4p):
1H NMR (300 MHz, CDCl ) δ: 1.28 (t, 3H, CH ), 4.17 (q, 2H, -O-CH2),
2.28 (d, 2H, CH2), 3.68 (s, 12H,3-OCH3), 4.19 (t, 1H3, CH), 4.57 (s, 1H, CH),
4.01(s, 1H, NH), 6.46–6.57 (m, 4H, HAr), 6.38-6.54 (m, 4H, HAr), 6.61-6.92
(m, 4H, HAr), 6.75-6.99 (m, 4H, HAr); IR (KBr, ν/cm–1): 3265, 1735, 1145,
1271, 1524; LC-MS (m/z): 594.16 (M+).
Ethyl
2,6-bis(4-chlorophenyl)-1-phenyl-4-(phenylamino)
tetrahydropyridine-3-carboxylate(4f):
1H NMR (300 MHz, CDCl3) δ: 1.32 (t, 3H, CH ),4.02 (q, 2H, -O-CH2),
2.37 (d, 2H, CH2), 4.09 (s, 1H, NH), 4.0 (t, 1H, CH),34.67 (s, 1H, CH), 6.51–
7.11 (m, 5H, HAr), 6.43–7.04 (m, 5H, HAr),6.73-6.97 (s, 4H, HAr), 6.67-6.97
(s, 4H, HAr); IR (KBr, ν/cm–1): 3307, 1743, 1540, 1152, 1210; LC-MS (m/z):
544.19 (M+).
ACKNOWLEDGEMENT
Methyl4-(4-methoxyphenylamino)-2,6-bis(4-bromophenyl)-1-(4-
methoxyphenyl) tetrahydro pyridine-3-carboxylate(4g):
The authors are thankful to the Head, Department of Chemical Technology,
Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431 004 (MS),
India, for providing the laboratory facility.
1H NMR (300 MHz, CDCl3) δ: 3.58 (s, 3H, O-CH ), 3.67 (s, 6H, OCH3),
4.1 (q, 2H, -O-CH ), 2.36 (d, 2H, CH2), 4.62 (s, 1H, 3CH),3.89(s, 1H, NH),
6.43–6.65 (m, 4H,2HAr), 6.33–6.55 (m, 4H, HAr),6.89-7.45 (m, 4H, HAr),
7.10-7.46 (m, 4H, HAr); IR (KBr, ν/cm–1): 3307, 1743, 1545, 1155, 1232;
LC-MS (m/z): 678.18 (M+).
REFERENCES
1. D. J. Ramón, and M. Yus, Angew. Chem. Int. Ed., 44, 1602 (2005).
2. H. Fujioka, K. Murai, O. Kubo, Y. Ohba, and Y. Kita, Org. Lett., 9, 1687
(2007).
3. K. Kumaravel, and G.Vasuki, Curr.Org. Chem., 13, 1820 (2009).
4. E. R. Bonfield, and C. J. Li, Adv. Synth. Catal., 350, 370 (2008).
5. I. Ugi, A. Domling, and B. J. Werner, Heterocycl. Chem., 37, 647 (2000).
6. C. O. Kappe, Eur. J. Med. Chem., 35, 1043 (2000).
7. D. Balan, and H. Adolfsson, Tet.Lett., 44, 2521 (2003).
8. G.Jones, Comprehensive Heterocyclic Chemistry, Pergamon, Oxford,
Vol. 2, (1984), p 482.
9. N. Elders, D. vanderBorn, L. J. D. Hendrickx, B. J .J. Timmer, A. Krause,
E. Janssen, F. J. J. de Kanter, E. Ruijter , and R. V. A. Orru, Angew. Chem.
Int. Ed., 48, 5856 (2009).
10. J. W. Daly, T. F. Spande, and H. M.Garraffo, J. Nat. Prod., 68, 1556
(2005).
Methyl-4-(4-methoxyphenylamino)-2,6-bis(3-chlorophenyl)-1,2,5,6-
tetrahydro-1-(4-methoxyphenyl)pyridine-3-carboxylate(4h):
1H NMR (300 MHz, CDCl3) δ: 3.72 (s, 3 H, -O-CH3), 2.27 (d, 2H, CH2),
3.69 (s, 6H, OCH3), 4.14 (t, 2H, CH2), 4.56 (s, 1H, CH), 3.92 (s, 1H, NH),
6.44–6.63 (m, 4H, HAr), 6.30–6.48 (m, 4H, HAr),6.97-7.04 (m, 4H, HAr),
7.03-7.19 (m, 4H, HAr); IR (KBr, ν/cm–1): 3276, 1736, 1547, 1167, 1256;
LC-MS (m/z): 588.11 (M+).
Methyl-4-(4-methoxyphenylamino)-2,6-bis(4-fluorophenyl)-1,2,5,6-
tetrahydro-1-(4-methoxyphenyl)pyridine-3-carboxylate(4i):
1H NMR (300 MHz, CDCl3) δ: 3.75 (s, 3H, -O-CH3), 2.23 (d, 2H, CH2),
3.70 (s, 6H, OCH3), 4.18 (t, 2H, CH2), 4.51 (s, 1H, CH), 3.98 (s, 1H, NH),
6.45–6.60 (m, 4H, HAr), 6.32–6.47 (m, 4H, HAr),6.89-7.01 (m, 4 H, HAr),
6.97-7.09 (m, 4H, HAr); IR (KBr, ν/cm–1): 3280, 1738, 1537, 1170, 1267;
LC-MS (m/z): 556.18 (M+).
Methyl-1,2,5,6-tetrahydro-2,6-bis(4-nitrophenyl)-1-phenyl-4-
(phenylamino)pyridine-3-carboxylate(4j):
11. M. Misra, S. K. Pandey, V. P. Pandey, J. Pandey, R. Tripathi, and R. P.
Tripathi, Bioorg. Med. Chem., 17, 625 (2009).
1H NMR (300 MHz, CDCl3) δ: 3.74 (s, 3H, -O-CH3), 2.39 (d, 2H, CH2),
4.09 (t, 1H, CH2), 4.57 (s, 1H, CH), 4.01 (s, 1H, NH), 6.58–7.02 (m, 5H, HAr),
6.41–6.95 (m, 5H, HAr), 7.29-8.01 (m, 4H, HAr), 7.33-8.09 (m, 4H, HAr);
IR (KBr, ν/cm–1): 3267, 1741, 1556, 1164, 1275, 1352, 1580; LC-MS (m/z):
550.12 (M+).
12. Y. Zhou, V. E. Gregor, B. K. Ayida, G. C. Winters, Z. Sun, D. Murphy,
G.Haley, D. Bailey, J. M. Froelich, S. Fish, S. E. Webber, T. Hermann,
and D. Wall, Bioorg. Med. Chem. Lett., 17, 1206 (2007).
13. S. Petit, J. P. Nallet, M. Guillard, J. Dreux, R. Chermat, M. Poncelet, C.
Bulach, P. Simon, C. Fontaine, M. Barthelmebs, and J. L. Imbs, Eur.J.Med.
Chem., 26, 19 (1991).
14. H. Bin, A. M. Crider, and J. P. Stables, Eur. J. Med. Chem., 36, 265 (2001).
15. M. Sales, and A. B. Charette, Org. Lett., 7, 5773 (2005).
16. R. M. Carballo, M. A. Ramirez, M. L. Rodriguez, V. S. Martin, and J. I.
Padron, Org. Lett., 8, 3837 (2006).
Methyl-1,2,5,6-tetrahydro-2,6-bis(3-nitrophenyl)-1-phenyl-4-
(phenylamino)pyridine-3-carboxylate(4k):
1H NMR (300 MHz, CDCl3) δ: 3.71 (s, 3H, -O-CH3), 2.36 (d, 2H, CH2),
4.09 (t, 1H, CH2), 4.61 (s, 1H, CH), 4.05 (s, 1H, NH), 6.57–6.96 (m, 5H, HAr),
6.49–7.07 (m, 5H, HAr), 7.38-8.00 (m, 4H, HAr), 7.39-8.02 (m, 4H, HAr);
IR (KBr, ν/cm–1): 3284, 1734, 1555, 1172, 1281, 1350, 1520; LC-MS (m/z):
550.12 (M+).
17. S. Fustero, D. Jimenez, J. Moscardo, S. Catalan, and C. D. Pozo, Org.
Lett., 9, 5283 (2007).
methyl-1,2,5,6-tetrahydro-2,6-bis(3-nitrophenyl)-1-phenyl-4-
(phenylamino)pyridine-3-carboxylate(4l):
18. F. A. Davis, B. Chao, and A. Rao, Org. Lett., 3, 3169 (2001).
19. A. T. Khan, T. Parvin, and L. H. Choudhury, J. Org. Chem., 73, 8393
(2008).
20. A. T. Khan, M. Lal, and M. M. Khan, Tet.Lett., 51, 4419 (2010).
21. A. T. Khan, M. M. Khan, and K. K. R. Bannuru, Tet. Lett., 66, 7762
(2010).
22. P. A. Clarke, A. V. Zaytzev, and A. C. Whitwood, Tet. Lett., 48, 5209
(2007).
23. C. Mukhopadhyay, S. R. Ray, J. Butcher, and A. M. Schmiedekamp, Tet.
Lett., 52, 5835 (2011).
1H NMR (300 MHz, CDCl3) δ: 3.69 (s, 3H, -O-CH3), 2.36 (d, 2H, CH2),
4.19 (t, 1H, CH), 4.6 (s, 1H, CH), 4.00 (s, 1H, NH), 6.56–7.02 (m, 5H, HAr),
6.47–7.02 (m, 5H, HAr), 7.40-7.98 (m, 4H, HAr), 7.43-8.04 (m, 4H, HAr);
IR (KBr, ν/cm–1): 3274, 1738, 1554, 1163, 1267, 1351, 1590; LC-MS (m/z):
550.19 (M+).
ethyl-4-(4-methoxyphenylamino)-2,6-bis(4-cyanophenyl)-1,2,5,6-
tetrahydro-1-(4-methoxyphenyl)pyridine-3-carboxylate(4m):
1H NMR (300 MHz, CDCl3) δ: 1.27 (t, 3H, CH3), 4.09 (q, 2H, -O-CH2),
2835