Rh(III)-Catalyzed C-H Amidation of 2-Arylindoles with Dioxazolones: A Route to Indolo[1,2- c]quinazolines

Xiaogang Wang; Jin Zhang; Di Chen; Bo Wang; Xiufang Yang; Yangmin Ma; Michal Szostak

doi:10.1021/acs.orglett.9b02615

Rh(III)-Catalyzed C-H Amidation of 2-Arylindoles with Dioxazolones: A Route to Indolo[1,2- c]quinazolines

Org Lett. 2019 Sep 6;21(17):7038-7043. doi: 10.1021/acs.orglett.9b02615. Epub 2019 Aug 22.

Authors

Xiaogang Wang¹, Jin Zhang¹, Di Chen^{1

2}, Bo Wang¹, Xiufang Yang¹, Yangmin Ma¹, Michal Szostak^{1

3}

Affiliations

¹ College of Chemistry and Chemical Engineering, Shaanxi Key Laboratory of Chemical Additives for Industry, Shaanxi University of Science and Technology, Xi'an 710021, China.
² School of Food and Biological Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China.
³ Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.

PMID: 31436105
DOI: 10.1021/acs.orglett.9b02615

Abstract

Rhodium(III)-catalyzed C-H amidation of 2-arylindoles with dioxazolones for the synthesis of indolo[1,2-c]quinazolines is reported. The reaction is compatible with a wide range of electronically diverse 2-arylindoles and dioxazolones, providing indolo[1,2-c]quinazolines in high to excellent yields. Most notably, the combination of this Rh-catalyzed C-H amidation and intramolecular N-H/N-C(O) cyclization enables the most straightforward direct route to indolo[1,2-c]quinazolines to date. Mechanistic studies and evaluation of antitumor activity of these high value heterocycles are disclosed.

Publication types

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