Process for the preparation of 4-substituted-1,4-dihydropydrines

Details Process for the preparation of 4-substituted-1,4-dihydropydrines Process for the preparation of 4-substituted-1,4-dihydropydrines

1992-07-28

1994-05-10

Waddell, Frederick E.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D21102

Patent

active

053109171

ABSTRACT:
4-Substituted-1,4-dihydropyridines are prepared by a cycloaddition reaction in which the cyclization is driven to completion, after thermal reaction, by addition of an acid. Felodipine, a vasodilator, is prepared by a cycloaddition reaction of ethyl 3-aminocrotonate with a suitably substituted dichlorobenzylidine under reaction conditions whereby the product crystallizes out of the reaction solution and may be directly isolated by filtration.

REFERENCES:
patent: 4264611 (1981-04-01), Berntsson et al.
patent: 4578395 (1986-03-01), Yamaguchi
patent: 4772596 (1988-09-01), Koike et al.
U. Eisner and J. Kuthan, Chem. Rev., 72, 1 (1972).
E. Klingsberg, ed. Pyridine and Its Derivatives: Part 1, pp. 435-455 (Interscience Publishers, N.Y. 1960).
J. Kuthan and A. Kurfurst, Ind. Eng. Chem. Prod. Res. Dev., 21, pp. 191-261 (1982).
A. Sausins and G. Duburs, Heterocycles, 27, pp. 269-289 (1988).
Streitwiser et al., Introduction to Organic Chemistry, pp. 272-275, 1097-1098 (MacMillan Publishing, Inc. 1976.).

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