Oxidative oxy-cyclization of 2-alkynylbenzamide enabled by TBAB/Oxone: switchable synthesis of isocoumarin-1-imines and isobenzofuran-1-imine

Literature Information

Publication Date 2019-04-01
DOI 10.1039/C9OB00320G
Impact Factor 3.876
Authors

Guanyinsheng Qiu, Hongwei Zhou, Jin-Biao Liu


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Abstract

A TBAB-catalyzed oxidative 6-endo-dig oxy-cyclization of 2-alkynylbenzamide is described herein for the synthesis of isocoumarin-1-imines. The transformation proceeds regioselectively and provides the final products with high efficiency and a broad reaction scope. Interestingly, an array of isobenzofuran-1-imines is also achieved under standard conditions when N-phenyl 2-trimethylsilylethynylbenzamides are used as substrates. Mechanism studies show that 3-bromomethenisobenzofuran-1-imine is a pivotal intermediate, which goes through C–O bond migration and debromination to offer the final isocoumarin-1-imines.

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