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Russian Journal of Organic Chemistry

, Volume 46, Issue 6, pp 894–897 | Cite as

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

  • N. T. Pokhodylo
  • V. S. Matiichuk
  • N. D. ObushakEmail author
Article

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.

Keywords

Ethyl Acetoacetate Cyclopropyl Ethyl Cyanoacetate MeONa Keto Ester 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  • N. T. Pokhodylo
    • 1
  • V. S. Matiichuk
    • 1
  • N. D. Obushak
    • 1
    Email author
  1. 1.Ivan Franko Lviv National UniversityLvivUkraine

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