Isomerization/recyclization of some 5-ethoxycarbonyl-pyrimidines

Ruben S Vardanyan, Victor J Hruby, G. G. Danagulyan, A. D. Mkrtchyan

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Abstract

This communication reports on the investigation of a new recyclization conversion of a pyrimidine ring, which can be referred to as C-C recyclization. In this reaction the nucleophile cleaves the pyrimidine ring at the N(3)-C(4) bond, and following rotation around the single C(5)-C(6) bond the new cyclization takes place. This type of recyclization has general applicability, and takes place upon alkali treatment of substituted 4-methyl-5-ethoxycarbonyl- and 4-amino-5-ethoxycarbonyl-pyrimidines (1) which are transformed respectively to 4-hydroxy-5-acetyl- and 4-hydroxy-5-carbamoylpyrimidines (2). The obtained pyrimidyl-ketones can be readily converted to their hydrazones 7-12.

Original languageEnglish (US)
Pages (from-to)557-562
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume42
Issue number4
Publication statusPublished - May 2005

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ASJC Scopus subject areas

  • Organic Chemistry

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