TANDEM CLEAVAGE OF 2,3,5-TRIMETHYL-7-TRIFLUOROACETYL-1,2,3,4-TETRAHYDROPYRROLO[1,2-<i>c</i>]PYRIMIDINE BY ACTIVATED ALKYNES, CAUSED BY MICHAEL ADDITION OF A TERTIARY NITROGEN ATOM TO A TRIPLE BOND

Authors

  • Л. Г. Воскресенский People's Friendship University of Russia, Moscow 117198
  • Т. Н. Борисова People's Friendship University of Russia, Moscow 117198
  • Л. Н. Куликова People's Friendship University of Russia, Moscow 117198
  • А. В. Варламов People's Friendship University of Russia, Moscow 117198

DOI:

https://doi.org/10.1007/7465

Keywords:

acetylenedicarboxylic ester, pyrrolopyrimidine, ethyl propiolate, tandem cleavage, zwitter-ion

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-trifluoro-acetylpyrroles. 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.

How to Cite
Voskressensky, L. G.; Borisova, T. N.; Kulikova, L. N.; Varlamov, A. V.  Chem. Heterocycl. Compd. 2007, 43, 913. [Khim. Geterotsikl. Soedin. 2007, 1082.]

For this article in the English edition see DOI 10.1007/s10593-007-0144-4


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Published

2023-02-16

Issue

No. 7 (2007)

Section

Original Papers