K2S2O8/TEMPO-Induced Cascade Oxidative Cyclization/1,2-Migration of Electron-Deficient Groups: Strategy for the Construction of 1 H-Pyrrol-2(3 H)-ones

Peng Gao; Juan Wang; Zijing Bai; Ming-Jin Fan; De-Suo Yang; Zheng-Hui Guan

doi:10.1021/acs.orglett.8b01402

K₂S₂O₈/TEMPO-Induced Cascade Oxidative Cyclization/1,2-Migration of Electron-Deficient Groups: Strategy for the Construction of 1 H-Pyrrol-2(3 H)-ones

Org Lett. 2018 Jun 15;20(12):3627-3630. doi: 10.1021/acs.orglett.8b01402. Epub 2018 Jun 4.

Authors

Peng Gao^{1

2}, Juan Wang¹, Zijing Bai¹, Ming-Jin Fan¹, De-Suo Yang¹, Zheng-Hui Guan²

Affiliations

¹ Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering , Baoji University of Arts and Sciences , Baoji , Shaanxi 721013 , P. R. China.
² Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science , Northwest University , Xi'an 710127 , P. R. China.

PMID: 29863885
DOI: 10.1021/acs.orglett.8b01402

Abstract

A K₂S₂O₈/TEMPO-induced oxidative cyclization of N-unprotected enaminoesters and enaminones that gave 1 H-pyrrol-2(3 H)-ones in good yields with broad functional group compatibility is reported. This method provides easy access to 1,2-carbon migration of ester or acyl group under transition-metal-free conditions.

Publication types

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