K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles

Xiaoming Zhu; Fuxing Zhang; Daizhi Kuang; Guobo Deng; Yuan Yang; Jiangxi Yu; Yun Liang

doi:10.1021/acs.orglett.0c00994

K₂S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles

Org Lett. 2020 May 15;22(10):3789-3793. doi: 10.1021/acs.orglett.0c00994. Epub 2020 May 3.

Authors

Xiaoming Zhu^{1

2}, Fuxing Zhang¹, Daizhi Kuang¹, Guobo Deng², Yuan Yang², Jiangxi Yu¹, Yun Liang²

Affiliations

¹ Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Hunan Province Universities Key Laboratory of Functional Organometallic Materials, College of Chemistry and Material Science, Hengyang Normal University, Hengyang, Hunan 421008, China.
² Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha, Hunan 410081, China.

PMID: 32362124
DOI: 10.1021/acs.orglett.0c00994

Abstract

We describe a three-component reaction of o-iodoanilines with K₂S and DMSO that provides 2-unsubstituted benzothiazoles in moderate to good isolated yields with good functional group tolerance. Electron-rich aromatic amines and o-phenylenediamines instead of o-iodoanilines provided 2-unsubstituted benzothiazoles and 2-unsubstituted benzimidazoles with and without K₂S under similar conditions. Notably, DMSO plays three vital roles: carbon source, solvent, and oxidant.