Reaction of N-fluoropyridinium fluoride with isonitriles and TMSN 3: a convenient one-pot synthesis of tetrazol-5-yl pyridines

Abstract

Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles and TMSN 3 led to the formation of the corresponding tetrazol-5-yl pyridines in good yields (37–84%). A similar reaction sequence for quinoline yielded the respective derivatives of 2-quinoline. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species.