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Furfuryl Cation Induced Cascade Formal [3 + 2] Cycloaddition/Double Ring-Opening/Chlorination: An Approach to Chlorine-Containing Complex Triazoles

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posted on 2018-11-09, 17:07 authored by Jiawei Guo, Xiaoming Xu, Qingzhao Xing, Ziwei Gao, Jing Gou, Binxun Yu
A TiCl4-promoted cascade formal [3 + 2] cycloaddition/double ring-opening/chlorination of 2-furylcyclobutanols with alkyl or aryl azides is described. This highly efficient transformation involves the formation/cleavage of several C–N, C–Cl, C–C, and C–O bonds in a single operation. It enables the quick construction of trisubstituted 1,2,3-triazoles with an (E)-enone moiety and a 3-chloropropyl unit. The chlorinated products are readily transformed into other structurally diverse analogues.

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