Terminal bis-acetylenes derived from 1,2-bis(1H-tetrazol-5-yl)ethane

Abstract

The N(1)—N(1), N(2)—N(2), and N(1)—N(2) regioisomers of 1,2-bis[(prop-2-yn-1-yl)-1H-tetrazol-5-yl]ethane were first synthesized by alkylation of 1,2-bis(1H-tetrazol-5-yl)ethane with propargyl bromide. The peculiarities of the crystal structure of 1,2-bis[1-(prop-2-yn-1-yl)-1H-tetrazol-5-yl]ethane were evaluated by X-ray diffraction analysis. This compound is readily underwent Cu-catalyzed [3+2] cycloaddition with p-tolyl azide, p-nitrophenyl azide, and benzyl azide to give heterocyclic assembles bearing 1,2,3-triazole and tetrazole cycles. Catalyst-free [3+2] cycloadditions of 1,2-bis[1-(prop-2-yn-1-yl)-1H-tetrazol-5-yl]ethane and the mixtures of the N(1)—N(1), N(2)—N(2), N(1)—N(2) regioisomers with poly(glycidyl azide) oligomers resulted in 1,2,3-triazole cycles and crosslinking of the polymer chains.