An efficient and regiospecific synthesis of 1,5-diaryl-4-benzothiazolyl-1,2,3-triazoles by organocatalytic 1,3-dipolar cycloaddition reactions

Abstract

An efficient synthesis of 1,5-diaryl-4-benzothiazolyl-substituted 1,2,3-triazoles by organocatalytic 1,3-dipolar cycloaddition reactions, from easily available benzo[d]thiazole derivatives and substituted azidobenzenes, has been developed. The 1,8-diazabicyclo[5,4,0]undec-7-ene is used as organocatalyst, and the 2-(1,5-diaryl-1H-1,2,3-triazol-4-yl)benzo[d]thiazoles were obtained in good yields (60% − 82%) with regiospecificity. The structures of all synthesized compounds were confirmed by ¹H NMR, ¹³C NMR and HRMS.

Graphical Abstract

Keywords:

• 1,2,3-triazoles
• benzo[d]thiazole derivatives
• organocatalytic 1,3-dipolar cycloaddition
• regiospecificity

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

We thank the National Natural Science Foundation of China [Grant 21702055] and the Youth Foundation of Hunan University [Grant 531107050885] for the financial support.