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Paper | Special issue | Vol 40, No. 2, 1995, pp.787-800
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S68
Synthesis of 5-Isopropenyl/Vinyl Substituted Pyrimidinones via[4+2] Cycloaddition Reactions of 1,3-Diaza-1,3-butadienes with Isopropenyl/Vinyl ketenes and Their Further Transformations: [4+2] and Unusual [3+2] cycloadditions with α-nitrosostyrenes

Arun K. Sharma and Mohinder P. Mahajan

*Department of Chemistry, North-Eastern Hill University, Shillong-793003, Meghalaya, India


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).