Copper-Catalyzed Synthesis of Polysubstituted Pyrroles through [3+1+1] Cycloaddition Reaction of Nitrones and Isocyanides

Zhuang Tian; Jiaojiao Xu; Bingxin Liu; Qitao Tan; Bin Xu

doi:10.1021/acs.orglett.8b00798

Copper-Catalyzed Synthesis of Polysubstituted Pyrroles through [3+1+1] Cycloaddition Reaction of Nitrones and Isocyanides

Org Lett. 2018 May 4;20(9):2603-2606. doi: 10.1021/acs.orglett.8b00798. Epub 2018 Apr 16.

Authors

Zhuang Tian¹, Jiaojiao Xu¹, Bingxin Liu¹, Qitao Tan¹, Bin Xu^{1

2}

Affiliations

¹ Department of Chemistry, Innovative Drug Research Center, School of Materials Science and Engineering , Shanghai University , Shanghai 200444 , China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , Shanghai 200032 , China.

PMID: 29659289
DOI: 10.1021/acs.orglett.8b00798

Abstract

An efficient, copper-catalyzed [3+1+1] cycloaddition reaction was developed for the expedient synthesis of pharmacologically interesting polysubstituted pyrroles from easily available nitrones and α-acidic isocyanides. The given approach features a new mode of cycloaddition between nitrones and isocyanides with wide substrate scope, good functional group tolerance, and operational simplicity. The operando infrared spectroscopy was used for the characterization of reaction intermediates.

Publication types

Research Support, Non-U.S. Gov't