Employing Arylacetylene as a Diene Precursor and Dienophile: Synthesis of Quinoline via the Povarov Reaction

作者:Yu, Xiao-Xiao; Zhao, Peng; Zhou, You; Huang, Chun; Wang, Li-Sheng; Wu, Yan-Dong*; Wu, An-Xin*
来源:Journal of Organic Chemistry, 2021, 86(12): 8381-8388.
DOI:10.1021/acs.joc.1c00793

摘要

A novel I-2-mediated Povarov reaction of arylacetylenes and anilines for the synthesis of 2,4-substituted quinolines has been developed, in which arylacetylene first acts as both a diene precursor and dienophile. This work further develops the Povarov reaction to expand the types of diene precursors. Preliminary mechanistic studies indicate that the I-2/DMSO system realized the oxidative carbonylation of C(sp)-H of arylacetylene and then undergoes a [4 + 2] cycloaddition reaction.