Multicomponent Coupling Reactions of Two N-Tosyl Hydrazones and Elemental Sulfur: Selective Denitrogenation Pathway toward Unsymmetric 2,5-Disubstituted 1,3,4-Thiadiazoles

Zhen Zhou; Yang Liu; Jiangfei Chen; En Yao; Jiang Cheng

doi:10.1021/acs.orglett.6b02583

Multicomponent Coupling Reactions of Two N-Tosyl Hydrazones and Elemental Sulfur: Selective Denitrogenation Pathway toward Unsymmetric 2,5-Disubstituted 1,3,4-Thiadiazoles

Org Lett. 2016 Oct 21;18(20):5268-5271. doi: 10.1021/acs.orglett.6b02583. Epub 2016 Sep 29.

Authors

Zhen Zhou¹, Yang Liu¹, Jiangfei Chen¹, En Yao¹, Jiang Cheng¹

Affiliation

¹ School of Petrochemical Engineering, Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, Jiangsu Province Key Laboratory of Fine Petrochemical Engineering, Changzhou University , Changzhou 213164, P. R. China.

PMID: 27684432
DOI: 10.1021/acs.orglett.6b02583

Abstract

A copper-mediated, three-component reaction between two different N-Ts hydrazones and elemental sulfur was developed, leading to a series of unsymmetric 2,5-disubstituted 1,3,4-thiadiazoles in moderate yields with good functional group compatibility. This procedure features the employment of elemental sulfur and the selective denitrogenation between aryl and alkyl aldehyde N-tosyl hydrazones, allowing rapid access to unsymmetric 2,5-disubstituted 1,3,4-thiadiazoles frameworks with chemical diversity and complexity.

Publication types

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