Novel domino products from the reaction of phenyl vinyl ketone and its derivatives with cyclic ketones

Article abstract of DOI:10.1016/S0040-4020(02)00091-1

Reaction of phenyl vinyl ketone with cyclopentanone under thermal conditions resulted in novel domino products, 1,5,9-triketones along with the expected 1,5-diketones. The 1,5,9-triketones were formed via a Michael-Michael-rearrangement pathway. On the other hand, reaction under basic conditions furnished a spiro[4.5]decanone, formed by domino pathways involving Michael-Michael-aldol condensation reactions. Microwave mediated reductive amination-cyclization of the 1,5,9-triketone furnished the perhydrocyclopenta[ij]quinolizine derivative.