Regioselective [4+2] cycloaddition versus nucleophilic reactions of N-arylamino substituted 1,3-diaza-1,3-butadienes with ketenes: Synthesis of pyrimidinone and fused pyrimidinone derivatives. Part II

Paramita D. Dey, Arun Sharma, Prasad V. Bharatam, Mohinder P. Mahajan

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Abstract

A novel synthetic method for 3-aryl-6-phenyl-2-methylthio/secondaryamino substituted-4(3H)-pyrimidinones 5 and 9 by the reactions of N-arylamino substituted 1,3-diaza-1,3-butadienes 1 and 6 with phenyl-, vinyl- and isopropenylketenes is explored. Semi emperical AM1 calculations on 1 and 6 are performed to explain the mechanism of their reaction with ketenes. Transformations of 5 and 9 leading to fused pyrimidinones 10 are also reported.

Original languageEnglish (US)
Pages (from-to)13829-13840
Number of pages12
JournalTetrahedron
Volume53
Issue number40
DOIs
Publication statusPublished - Oct 6 1997

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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