An Efficient Synthesis of 4-Aryl-1,4-dihydropyridines
Letters in Organic Chemistry, 2011, Vol. 8, No. 10
711
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factorial design studies. Am. J. Cardiovasc. Drugs, 2006, 6,
103-113.
Cooper, K., Fray, M. J., Parry, M. J., Richardson, K.,
Steele, J. 1,4-Dihydropyridines as antagonists of platelet
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3i: H NMR (CDCl3, 400MHz, ppm) ꢀ= 6.92-6.76 (m,
3H), 5.87(bs, 1H), 5.53 (s, 1H) 4.92(s, 1H), 4.14 (q, 4H),
3.81 (s, 3H), 2.28 (s, 6H), 1.25 (t, 6H). IR(KBr) ꢁ = 3353,
2976, 2902, 2807, 1651, 1560, 1487 cm-1
[7]
1
3j: H NMR (CDCl3, 400MHz, ppm) ꢀ=7.24-6.79 (m,
4H), 5.62 (brs, 1H), 5.40 (s, 1H), 5.04 (s,1H), 4.15 (q, 4H),
2.33 (s, 6H), 1.27 (t, 6H); IR (KBr) ꢁ =3349, 2985, 2935,
1662, 1628, 1514, 1485, 1362, 1315, 1228, 1170, 1022, 854,
763cm-1.
[8]
[9]
McInally, T.; Tinker, A. C. A novel, base-induced
fragmentation of Hantzsch-type 4 -aryl-1, 4- dihydropyri-
dines. J. Chem. Soc., Perkin Trans. 1, 1988, 7, 1837-1844.
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4-aryl-1,4-dihydropyridines via the Hantzsch three
component condensation. Tetrahedron Lett., 2000, 41,
4311-4315.
Sabitha, G., Kiran, G. S., Reddy, C. S., Yadav, J. S. A novel
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4131.
Lei, M., Ma, L., Hu, L. A convenient one-pot synthesis of
formamide derivatives using thiamine hydrochloride as a
novel catalyst. Tetrahedron Lett., 2010, 51, 4186-4188.
Lei, M., Ma, L., Hu, L. VB1-Al2O3-catalyzed one-pot
condensation of aromatic ketone, aromatic aldehyde, and
amide. Tetrahedron Lett., 2010, 51, 4746-4749.
General Procedure for Synthesis of 1,4-dihydropyridines:
Ethyl acetoacetate (10 mmol) was added dropwise to
aromatic aldehydes (5 mmol) in 50 mL flask, then NH4OAc
(5 mmol) and VB1 (5% mol) was added to the above
mixture at room temperature. Then the mixture was
irradiated in microwave (375W) in an open flask for 2-
3min. The reaction mixture left to cool to room temperature
and added 10ml water, the mixture was filtered and given
crude product, the title compound was recrystallized from
appropriate solvent to analytical purity.
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3k: H NMR (CDCl3, 400MHz, ppm) ꢀ= 7.19 -6.12 (m,
3H), 5.76(s, 1H), 5.32 (s, 1H) 4.42(q, 4H), 2.34(s, 6H),
1.28(t, 6H). IR(KBr) ꢁ = 3349, 2980, 1680, 1652, 1590,
1514 cm-1.
[10]
1
3l: H NMR (CDCl3, 400MHz, ppm) ꢀ=7.84-7.43(m,
3H), 5.73(s, 1H), 5.34(s, 1H), 4.38(q, 4H), 2.31(s, 3H), 1.33
(t, 6H).IR(KBr) ꢁ =3344, 3109, 2979, 1692, 1656, 1487,
1369, 1329, 1260, 1301, 1211, 1155, 854, 722 cm-1.
[11]
[12]
[13]
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