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

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...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2010-06, Vol.46 (6), p.894-897
Main Authors: Pokhodylo, N. T, Matiichuk, V. S, Obushak, N. D
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary: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.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428010060199