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Metal-Free C-H [5 + 1] Carbonylation of 2-Alkenyl/Pyrrolylanilines Using Dioxazolones as Carbonylating Reagents

Jiang Nan*, Pu Chen, Xue Gong, Yan Hu, Qiong Ma, Bo Wang and Yangmin Ma

*College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China, Email: nanjiangsust.edu.cn

J. Nan, P. Chen, X. Gong, Y. Hu, Q. Ma, B. Wang, Y. Ma, Org. Lett., 2021, 23, 3761-3766.

DOI: 10.1021/acs.orglett.1c01147 (free Supporting Information)


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Abstract

A metal-free CH [5 + 1] carbonylative annulation of 2-alkenyl/pyrrolylanilines with dioxazolones as carbonylating reagents provides privileged quinolinones and pyrrolyl-fused quinoxalinones. This process features exceedingly simple operation and tolerates both vinyl and aryl substrates. Formation of an isocyanate intermediate plays a crucial role in the carbonylation annulation.


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proposed mechanism



Key Words

2-quinolones


ID: J54-Y2021