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

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.