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Published on: June 29, 2014
Furfuryl Cation Induced Cascade Formal [3 + 2] Cycloaddition/Double Ring-Opening/Chlorination: An Approach to
Jiawei Guo1, Xiaoming Xu1, Qingzhao Xing1
1Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry & Chemical Engineering, Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical , Shaanxi Normal University , Xi'an 710062 , China.
Abstract:
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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