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Switchable Synthesis of 3-Substituted 1H-Indazoles and 3,3-Disubstituted 3H-Indazole-3-phosphonates Tuned by Phosphoryl Groups

Guihua Chen, Minglin Hu and Yungui Peng*

*Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. China, Email: pygswu.edu.cn

G. Chen, M. Hu, Y. Peng, J. Org. Chem., 2018, 83, 1591-1597.

DOI: 10.1021/acs.joc.7b02857 (free Supporting Information)


Abstract

1,3-Dipolar cycloaddition reactions between α-substituted α-diazomethylphosphonates and arynes provide 3-alkyl/aryl-1H-indazoles and 3-alkyl/aryl-3H-indazole-3-phosphonates efficiently under simple reaction conditions. The phosphoryl group acted both as a tuning group and a traceless group.


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proposed mechanism



Key Words

indazoles, 1,3-dipolar cycloaddition


ID: J42-Y2018