Efficient Assembly of Chromone Skeleton from 2,3-Allenoic Acids and Benzynes

Abstract

Chromone derivatives were synthesized from 2,3-allenoic acids and benzynes in moderate to excellent yields under mild conditions. Instead of the cyclic conjugate addition of the intermediate A formed by the nucleophilic addition of allenoic acid with benzyne, this intermediate undergoes 1,2-addition with the carbonyl group, which was followed by the ring opening, conjugate addition, and protonolysis to afford chromone derivatives. This protocol allows the diversity due to the substituent-loading capability of 2,3-allenoic acids as well as benzynes