Unexpected O → S and N → S alkyl transfer reactions in the reaction of 3-alkyl-2-(N-cyanoimino)thiazolidines with sodium alkoxides: a new synthesis of cimetidine

Unexpected O → S and N → S alkyl transfer reactions were observed in the reaction of 3-alkyl-2-(N-cyanoimino)thiazolidines with sodium alkoxides, and a new synthetic method for cimetidine was developed using the N → S alkyl transfer reaction as a key step.