Tunable base-controlled chemoselective synthesis of trifluoromethyl-containing N-substituted benzimidazole-2-thiones and monofluorinated 4 H-benzo[4,5]imidazo[2,1- b][1,3]thiazine

Yupian Deng; Yuhao Qian; Jiaqi Huang; Zhudi Sun; Ronghua Zhuge; Qingchun Huang; Song Cao

doi:10.1039/d4ob01999g

Tunable base-controlled chemoselective synthesis of trifluoromethyl-containing N-substituted benzimidazole-2-thiones and monofluorinated 4 H-benzo[4,5]imidazo[2,1- b][1,3]thiazine

Org Biomol Chem. 2025 Jan 8. doi: 10.1039/d4ob01999g. Online ahead of print.

Authors

Yupian Deng¹, Yuhao Qian¹, Jiaqi Huang¹, Zhudi Sun¹, Ronghua Zhuge¹, Qingchun Huang¹, Song Cao¹

Affiliation

¹ Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology (ECUST), Shanghai 200237, China. [email protected].

PMID: 39776113
DOI: 10.1039/d4ob01999g

Abstract

A highly efficient base-controlled synthesis of N-β-trifluoromethyl-substituted 2H-benzo[d]imidazole-2-thiones and 2-fluoro-4H-benzo[4,5]imidazo[2,1-b][1,3]thiazines via hydroamination or defluorinative cyclizations of α-(trifluoromethyl)styrenes with 2-mercaptobenzimidazole was developed.