NJC
Paper
of methanol at room temperature. After 20 min aromatic (2H, d, J = 8Hz, ArH), 6.63–6.60 (1H, t, J = 7.5 Hz, ArH), 7.12–7.06
aldehyde (2 mmol) was added to the reaction mixture and (5H, m, ArH), 7.25–7.17 (3H, m, ArH), 7.33–7.26 (5H, m, ArH), 7.39–
stirring was continued until the completion of the reaction 7.35 (2H, d, J = 20 Hz, ArH), 10.31 (1H, s, NH); 13C NMR (125 MHz,
(monitored by TLC). The solid precipitates were filtered off and CDCl3): d = 14.9, 33.7, 55.2, 58.3, 59.8, 98.4, 113.1, 116.3, 125.7,
washed with ethanol to afford nearly the pure products. The 125.9, 126.4, 126.5, 126.7, 127.2, 128.3, 128.7, 128.9, 129.0, 138.0,
solid products were further purified by recrystallization in 142.9, 144.2, 147.1, 156.1, 168.3; anal. calcd for C32H30N2O2: requires
ethanol.
Methyl 2,6-bis(3-methoxyphenyl)-1-phenyl-4-(phenylamino)-
C, 80.98; H, 6.37; N, 5.90%, found C, 80.83; H, 6.32; N, 6.04%.
1,2,5,6-tetrahydropyridine-3-carboxylate (10c). White solid,
m.p.: 221–223 1C; 1H (500 MHz, CDCl3) d = 2.80 (1H, dd,
J = 15.2, 2.4 Hz, H-500), 2.95 (1H, dd, J = 15.2, 5.6 Hz, H-50),
Acknowledgements
MMK is thankful to UGC, New Delhi, for Grant [F-20-1/
2012(BSR)/20-2(15)/2012(BSR)]. The authors are grateful to the
UGC, New Delhi, for providing financial support. The authors
would also like to thank SAIF, PU, Chandigarh and CLRI,
Chennai, for providing NMR spectra. We are also thankful
to the Department of Chemistry, AMU, Aligarh, for providing
basic infrastructures.
3.76 (3H, s, ArOMe), 3.79 (3H, s, ArOMe), 3.92 (3H, s, C(O)OMe),
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5.10 (1H, d, J = 3.2 Hz, H-6), 6.35 (2H, d, J = 7.9 Hz, ArH), 6.39
(1H, s, H-2), 6.54 (2H, d, J = 8.0 Hz, ArH), 6.62 (1H, t, J = 7.2 Hz,
ArH), 6.79 (4H, d, J = 8.8 Hz, ArH), 7.08 (2H, d, J = 8.4 Hz, ArH),
7.10 (2H, d, J = 8.8 Hz, ArH), 7.12 (1H, t, J = 7.2 Hz, ArH), 7.18
(2H, d, J = 7.2 Hz, ArH), 7.26 (2H, d, J = 8.8 Hz, ArH), 10.26
(1H, s, NH); 13C (100 MHz, CDCl3) d = 32.48, 49.96, 54.05, 54.10,
54.19, 57.13, 96.62, 110.00, 110.77, 111.78, 111.95, 112.02,
115.23, 117.82, 118.07, 124.78, 124.94, 127.80, 128.12, 128.60,
136.85, 143.56, 144.87, 145.88, 155.36, 158.61, 158.90, 167.47;
anal. calcd for C33H32N2O4: requires C, 76.13; H, 6.20; N, 5.38%.
Found: C, 75.98; H, 6.08; N, 5.24%.
Notes and references
1 (a) J. Zhu and H. Bienayme, Multicomponent Reactions,
Wiley-VCH, Weinheim, Germany, 1st edn, 2005; (b) P. A.
Tempest, Curr. Opin. Drug Discovery Dev., 2005, 8, 776;
Methyl 2,6-bis(4-ethylphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-
tetrahydropyridine-3-carboxylate (10h). White solid, m.p.: 196–
198 1C; IR (KBr, cmꢁ1): n = 1655 (CQO), 1593 (CQC); 1H
¨
´
(c) A. Domling, Chem. Rev., 2006, 106, 17; (d) D. J. Ramon
¨
and M. Yus, Angew. Chem., 2005, 117, 1628; (e) A. Domling
(500 MHz, CDCl3) d = 1.22 (3H, t, J = 7.6, CH2CH3), 2.64 (2H, q,
and I. Ugi, Angew. Chem., Int. Ed., 2000, 39, 3168;
( f ) A. T. Khan and M. M. Khan, Tetrahedron Lett., 2011,
52, 3455.
2 S. Maddila, S. Rana, R. Pagadala, S. Kankala, S. N. Maddila
and S. B. Jonnalagadda, Catal. Commun., 2015, 61, 26.
3 (a) B. M. Trost, Science, 1991, 254, 1471; (b) B. M. Trost,
Angew. Chem., Int. Ed. Engl., 1995, 34, 259.
4 (a) E. S. Putilova, G. V. Kryshtal, G. M. Zhdankina,
N. A. Troitskii and S. G. Zlotin, Russ. J. Org. Chem., 2005,
41, 512; (b) F. Dong, F. Zhenghao and L. Zuliang, Catal.
Commun., 2009, 10, 1267.
5 L. H. Choudhary and T. Parveen, Tetrahedron, 2011,
67, 8213.
6 (a) F. Jahani, B. Zamenian, S. Khaksar and M. Tajbakhsh,
Synthesis, 2010, 3315; (b) W. Zhou, L. W. Xu, L. Yang,
P. Q. Zhao and C. G. Xia, J. Mol. Catal. A: Chem., 2006,
249, 129.
7 M. Lal, R. S. Basha, S. Sarkar and A. T. Khan, Tetrahedron
Lett., 2013, 54, 4264.
8 (a) P. Yu, G. Liu and R. Tang, Curr. Organocatal., 2014, 1, 79;
(b) B. Ay, S. Karaca, E. Yildiz, V. Lopez, M. H. Nanao and
J. Zubieta, J. Solid State Chem., 2016, 233, 415.
9 (a) Y. Z. Ye, S. Lin and X. J. Wu, Chin. J. Struct. Chem., 2014,
33, 1649; (b) A. Yogananth and S. S. Mansoor, Pharma
Chem., 2015, 7, 105.
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J = 7.6 Hz, CH2CH3), 2.72 (1H, dd, J = 15.2, 2.4 Hz, H-500), 2.86 (1H,
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dd, J = 15.2, 5.6 Hz, H-50), 3.93 (3H, s, OMe), 5.13 (1H, d, J = 3.2 Hz,
H-6), 6.26 (2H, d, J = 8.0 Hz, ArH), 6.44 (1H, s, H-2), 6.57 (2H, d, J =
8.0 Hz, ArH), 6.60 (1H, t, J = 7.2 Hz, ArH), 7.05–7.13 (1H, m, ArH),
7.22 (2H, d, J = 8.0 Hz, ArH), 10.24 (1H, s, NH); 13C (100 MHz,
CDCl3) d = 14.39, 14.84, 27.35, 27.54, 32.61, 49.93, 53.87, 57.03,
97.06, 111.87, 114.93, 124.66, 124.94, 125.30, 125.56, 126.65,
127.08, 127.18, 127.73, 136.91, 139.08, 140.06, 141.05, 142.16,
146.02, 155.5, 167.62; anal. calcd For C35H36N2O2: requires C,
81.36; H, 7.02; N, 5.42%, found C, 81.13; H, 6.83; N, 5.51%.
Methyl 1-phenyl-4-(phenylamino)-2,6-di(thiophen-2-yl)-1,2,5,6-
tetrahydropyridine-3-carboxylate (10m). White solid, m.p.: 211–
213 1C; IR (KBr, cmꢁ1): n = 3435 (N–H), 1656 (CQO), 1614 (CQC);
1H NMR (500 MHz, CDCl3): d = 2.97–2.87 (2H, m, H-50 and H-500),
3.75 (3H, s, OMe), 4.92–4.89 (1H, dd, J = 15, 5 Hz, H-6), 6.18
(1H, s, H-2), 6.80–6.77 (1H, t, J = 15 Hz, ArH), 6.84–6.82 (1H, t, J =
10 Hz, ArH), 7.07–6.97 (7H, m, Ar), 7.20–7.13 (4H, m, Ar), 7.25–
7.24 (1H, d, J = 5 Hz, Ar), 7.33–7.30 (2H, t, J = 10 Hz, Ar), 10.60 (1H,
s, NH); 13C NMR (125 MHz, CDCl3): d = 37.1, 51.2, 56.1, 59.7, 98.6,
116.5, 119.4, 124.12, 124.17, 124.23, 124.27, 124.7, 125.3, 126.6,
127.2, 128.9, 129.5, 138.4, 148.5, 150.1, 152.8, 157.4, 168.3; anal.
calcd for C27H24N2O2S2: requires C, 68.62; H, 5.12; N, 5.93%,
found C, 68.51; H, 5.15; N, 5.86%.
Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-
3-carboxylate (10n). White solid, m.p.: 169–171 1C; IR (KBr, cmꢁ1): 10 E. Bellur and P. Langer, Tetrahedron Lett., 2006, 47, 2151.
1
n = 3435 (N–H), 1652 (CQO), 1593 (CQC); H NMR (500 MHz, 11 S. S. Tarnavsky, G. G. Dubinina, S. M. Golovach and
CDCl3) d = 1.49–1.47 (3H, t, J = 10 Hz, OCH2CH3), 2.88–2.77 (2H, m,
S. M. Yarmoluk, Biopolym. Cell, 2003, 19, 548.
H-500 and H-50), 5.17 (1H, s, H-6), 4.50–4.33 (2H, m), 6.31–6.29 12 T. K. Hinio, T. G. Machida, A. K. Hino, A. Y. Oume and
(2H, dd, J = 8 and 2 Hz, ArH and H-2), 6.48 (1H, s, ArH), 6.55–6.54 H. M. Hachioji, US Pat., 1990, vol. 828, p. 4909.
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