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Methyl 3-cyclopropyl-3-oxopropanoate in the synthesis of heterocycles having a cyclopropyl substituent

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Abstract

Reactions of methyl 3-cyclopropyl-3-oxopropanoate with chloroacetone and ammonia, benzaldehyde and ammonia, and benzoquinone gave, respectively, methyl 2-cyclopropyl-5-methyl-1H-pyrrole-3-carboxylate, dimethyl 2,6-dicyclopropyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate, and methyl 2-cyclopropyl-5-hydroxy-1-benzofuran-3-carboxylate. Cyclization of methyl 3-cyclopropyl-3-oxopropanoate with ethyl chloro(arylhydrazono)ethanoates and other halohydrazones led to the formation of 3-substituted 1-aryl-5-cyclopropyl-1H-pyrazole-4-carboxylic acids, and 5-cyclopropyl-1-(quinolin-5-yl)-1H-1,2,3-triazole-4-carboxylic acid was obtained by reaction of the title compound with 5-azidoquinolines.

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Correspondence to N. D. Obushak.

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Original Russian Text © N.T. Pokhodylo, V.S. Matiichuk, N.D. Obushak, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 6, pp. 898–901.

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Pokhodylo, N.T., Matiichuk, V.S. & Obushak, N.D. Methyl 3-cyclopropyl-3-oxopropanoate in the synthesis of heterocycles having a cyclopropyl substituent. Russ J Org Chem 46, 894–897 (2010). https://doi.org/10.1134/S1070428010060199

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  • DOI: https://doi.org/10.1134/S1070428010060199

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