Ring opening and ring expansion of 8-cyano-tetrazolo[1,5-a]pyridine with secondary amines. Reactions of azides, tetrazoles and nitrenes with nucleophiles, Part 2

Abstract

8-Cyanotetrazolo[1,5-a]pyridine 6T undergoes photochemical ring expansion to afford 1,3-diazepine 7 with diisopropylamine, but with stronger nucleophiles such as dimethylamine a rapid, quantitative ring opening reaction affords dienyltetrazoles 8 and 9 in the dark (an Addition of Nucleophile -Ring Opening reaction).