Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles

Wei-Li Chen; Si-Yi Wu; Xue-Ling Mo; Liu-Xu Wei; Cui Liang; Dong-Liang Mo

doi:10.1021/acs.orglett.8b01294

Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles

Org Lett. 2018 Jun 15;20(12):3527-3530. doi: 10.1021/acs.orglett.8b01294. Epub 2018 May 25.

Authors

Wei-Li Chen¹, Si-Yi Wu¹, Xue-Ling Mo¹, Liu-Xu Wei¹, Cui Liang¹, Dong-Liang Mo¹

Affiliation

¹ State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China; School of Chemistry and Pharmaceutical Sciences , Guangxi Normal University , 15 Yu Cai Road , Guilin , 541004 , China.

PMID: 29798675
DOI: 10.1021/acs.orglett.8b01294

Abstract

A variety of 2-aminobenzonitriles were prepared from 2-arylindoles in good to excellent yields through tert-butylnitrite (TBN)-mediated nitrosation and sequential iron(III)-catalyzed C-C Bond cleavage in a one-pot fashion. The 2-aminobenzonitriles can be used to rapidly synthesize benzoxazinones by intramolecular condensation. The present method features an inexpensive iron(III) catalyst, gram scalable preparations, and novel C-C bond cleavage of indoles.

Publication types

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