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Synthesis of ethoxycarbonyl-1,4- and -1,2-dihydropyridinecarboxylic acid amides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

3-Carbamoyl derivatives of 4-phenyl-5-ethoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine were obtained by cyclocondensation of 2-benzylideneacetoacetic ester with Β-aminocrotonic acid amide or anilides. In the alkylation of 4-phenyl-5-ethoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid anilides the amido group is initially alkylated, after which the ring NH group is alkylated, while the thiocarbamoyl group is converted to a cyano group. Reduction of the pyridinium salts gave 3- and 5-carbamoyl derivatives of 4-phenyl-1,2,6-trimethyl-1,2-dihydropyridine-5- and -3-carboxylic acids.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1665–1673, December, 1991.

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Zandersons, A., Lusis, V., Vigante, B. et al. Synthesis of ethoxycarbonyl-1,4- and -1,2-dihydropyridinecarboxylic acid amides. Chem Heterocycl Compd 27, 1339–1347 (1991). https://doi.org/10.1007/BF00515579

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  • DOI: https://doi.org/10.1007/BF00515579

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