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Cu-Catalyzed Denitrogenative Transannulation of 3-Aminoindazoles To Assemble 1-Aminoisoquinolines and 3-Aminobenzothiophenes

Yao Zhou, Ya Wang, Yixian Lou and Qiuling Song*

*Institute of Next Generation Matter Transformation, College of Materials Science & Engineering at Huaqiao University, 668 Jimei Boulevard, Xiamen, Fujian 361021, China, Email: qsonghqu.edu.cn

Y. Zhou, Y. Wang, Y. Lou, Q. Song, Org. Lett., 2019, 21, 8869-8873.

DOI: 10.1021/acs.orglett.9b02288 (free Supporting Information)



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Abstract

A Cu-catalyzed denitrogenative transannulation of 3-aminoindazoles provides diverse functionalized 3-aminobenzothiophenes and 1-aminoisoquinolines. This transformation proceeds via an "extrude-and-sew" strategy with an unprecedented radical reactivity of 3-aminoindazoles.

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proposed mechanism

synthesis of aminobenzothiophenes (see article for more examples)



Key Words

isoquinolines, TBHP


ID: J54-Y2019