Synthesis of 5-isopropenyl/vinyl substituted pyrbvddinones via [4+2] cycloaddition reactions of 1,3-diaza-1,3-butadienes with isopropenyl/vinylketenes and their further transformations: [4+2] and unusual [3+2] cycloadditionsw α-nitrosostyrenes

Arun Sharma, Mohinder P. Mahajan

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1.3-Diaza-1.3-butadienes (1 and 5) underwent [4+2] cycloaddition reactions with isopropenyl/vinylketenes (2), acting as 2π components, to result in pyrimidinones (4 and 7). The treatment of 5-isopropenyl substituted pyrimidinones with phosphorus pentasulfide in the presence of sodium carbonate in dry tetrahydrofuran gave pyrimidinones (8). The reactions of nitrosoalkenes with 5-vinyl substituted pyrimidinones resulted in [4+2] cycloadditions leading to 1,2-oxazines (15), whereas 5-isopropenyl substituted pyrimidinones resulted in unusual [3+2] cycloaddition reactions yielding the nitrones (14).

Original languageEnglish (US)
Pages (from-to)787-800
Number of pages14
Issue number2
Publication statusPublished - Mar 1 1995


All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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