Lewis Acid Mediated Tandem Reaction of Propargylic Alcohols to Tetrazoles Involving C-O- and C-C-Bond Cleavage Reactions and a C-N-Bond Formation

摘要

A novel and direct synthesis of 1-aryl-5-arylvinyltetrazoles from easily prepared propargylic alcohols and TMSN_3 is developed in the presence of TMSCl under mild conditions (TMS=trimethylsilyl). The process involves an allenylazide intermediate, followed by a C-C-bond cleavage and C-N-bond formation to afford the desired products. Moreover, this method offers a good functionalgroup applicability and can be scaled-up to grams (yield up to 85 ).