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Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
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Org. Biomol. Chem., 2012,10, 7739-7746
07 Jul 2012,
02 Aug 2012
First published online
02 Aug 2012
DABCO-catalyzed [4 + 2] and Bu3P-catalyzed [3 + 2] cycloadditions between 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate were developed for the synthesis of dihydropyran-fused and cyclopenten-fused chromen-2-ones with high regio- and stereo-selectivities, respectively. The synthetic procedures have the advantages of mild reaction conditions, convenient handling and good atom economy as well as a wide substrate scope, which make this method useful for the synthesis of potentially biologically active dihydropyran-fused and cyclopenten-fused chromen-2-ones derivatives. Possible reaction mechanisms have also been proposed on the basis of previous literature and our investigation.