L-Proline catalyzed one-step synthesis of 4,5-diaryl-2 H-1,2,3-triazoles from heteroaryl cyanostilbenes via [3+2] cycloaddition of azide

Tetrahedron Lett. 2014 Oct 1;55(40):5562-5565. doi: 10.1016/j.tetlet.2014.08.027.

Abstract

Use of a novel reagent has been established for the synthesis of a series of 4,5-diaryl-2H-1,2,3-triazoles (6a-i and 9a-e) from cyanostilbene analogs of benzo[b]thiophene, benzo[b]furan and indole, catalyzed by L-proline via Lewis base-catalyzed one-step [3+2]cycloaddition of azide. This method provides an efficient, simple and environmentally benign procedure that affords good yields and relatively short reaction times.

Keywords: 4,5-Diaryl-2H-1,2,3-triazoles; Heteroaryl cyanostilbenes; L-Proline; Sodium azide; [3+2] Cycloaddition of azide.