Rh(III)-Catalyzed [4 + 2] Annulation of Indoles with Diazo Compounds: Access to Pyrimido[1,6-a]indole-1(2H)-ones

Xun Chen; Xinwei Hu; Siyi Bai; Yuanfu Deng; Huanfeng Jiang; Wei Zeng

doi:10.1021/acs.orglett.5b03231

Rh(III)-Catalyzed [4 + 2] Annulation of Indoles with Diazo Compounds: Access to Pyrimido[1,6-a]indole-1(2H)-ones

Org Lett. 2016 Jan 15;18(2):192-5. doi: 10.1021/acs.orglett.5b03231. Epub 2015 Dec 28.

Authors

Xun Chen¹, Xinwei Hu¹, Siyi Bai¹, Yuanfu Deng¹, Huanfeng Jiang¹, Wei Zeng¹

Affiliation

¹ School of Chemistry and Chemical Engineering, South China University of Technology , Guangzhou 510641, China.

PMID: 26710082
DOI: 10.1021/acs.orglett.5b03231

Abstract

The Rh(III)-catalyzed regioselective C2-H bond carbenoid insertion/cyclization of N-amidoindoles with α-acyl diazo compounds has been developed. This method provides a novel approach to 2H-pyrimido[1,6-a]indol-1-ones with a broad range of functional group tolerance. The synthetic utilities of the approach are demonstrated by versatile chemical transformations.

Publication types

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