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

• DOI: 10.1021/acs.orglett.8b03121
• Publication Date: 2018-11-09T18:45:50Z
• Authors: Jiawei Guo; Xiaoming Xu; Qingzhao Xing; Ziwei Gao; Jing Gou; Binxun Yu
• Keywords: Formal synthesis

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 several C-N, C-Cl, C-C, and C-O bonds in a single operation. It enables quick construction trisubstituted 1,2,3-triazoles an ( E)-enone moiety 3-chloropropyl unit. The chlorinated products are readily transformed into other structurally diverse analogues.