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Chemistry of Heterocyclic Compounds

, Volume 43, Issue 7, pp 913–918 | Cite as

Tandem cleavage of 2,3,5-trimethyl 7-trifluoroacetyl-1,2,3,4-tetrahydro-pyrrolo[1,2-c]pyrimidine by activated alkynes, caused by Michael addition of a tertiary nitrogen atom to a triple bond

  • L. G. Voskressensky
  • T. N. Borisova
  • L. N. Kulikova
  • A. V. Varlamov
Article

Abstract

The interaction of 7-trifluoroacetyltetrahydropyrrolo[1,2-c]pyrimidine with acetylenedicarboxylic ester (DMAD) and ethyl propiolate in acetonitrile and alcohols has been studied. It was established that DMAD splits pyrrolopyrimidine at the aminal fragment in acetonitrile and methanol with the formation of 1-H-and 2-(N-dimethoxycarbonylvinyl-N-methyl)aminoethyl-1-methoxymethyl-3-methyl-5-trifluoroacetylpyrroles. In acetonitrile ethyl propiolate splits pyrrolopyrimidine both at the aminal fragment and at the C(3)-N(2) bond (Hofmann reaction), but in ethanol only at the C(3)-N(2) bond with the formation of 2-propenylpyrroles.

Keywords

acetylenedicarboxylic ester pyrrolopyrimidine ethyl propiolate tandem cleavage zwitterion 

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • L. G. Voskressensky
    • 1
  • T. N. Borisova
    • 1
  • L. N. Kulikova
    • 1
  • A. V. Varlamov
    • 1
  1. 1.People’s Friendship University of RussiaMoscow

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