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Short Paper | Regular issue | Vol 94, No. 9, 2017, pp.1775-1782
Published online, 6th July, 2017
DOI: 10.3987/COM-17-13763
Synthesis of Fused 1,2,3-Triazoles through Carbocation-Mediated Intramolecular [3+2] Cycloaddition of Azido-propargyl Alcohols

Youlai Zhang, Junru Li, Mengdi Wang, Huan Zhang,* Hiroki Tanimoto, Tsumoru Morimoto, and Kiyomi Kakiuchi

*Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P.R. China

Abstract

A practical and efficient intramolecular cyclization reaction with azido-propargyl cations is described. Range of acids and activating reagents were selected to demonstrate the reaction conditions. Organic azides and propargyl cations generated by toluenesulfonic acid gave fused 1,2,3-triazoles undergo metal-free intramolecular azide–alkyne [3+2] cycloaddition reactions. Various fused triazoles were obtained within 30 min in good yields under mild reaction conditions.