Synthesis of imidazo[4,5- e][1,3]thiazino[2,3- c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5- e]thiazolo[2,3- c][1,2,4]triazines

Abstract

A series of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines was synthesized via a cascade sequence of hydrolysis and skeletal rearrangement of imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazin-7(8H)-ylidene)acetic acid esters in methanol upon treatment with excess KOH. Imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazin-6(7H)-ylidene)acetic acid esters are also suitable substrates for the reaction. In this case hydrolysis and thiazole ring expansion were accompanied with the change of the thiazolotriazine junction type from thiazolo[3,2-b][1,2,4]triazine to thiazino[2,3-c][1,2,4]triazine.

Keywords: 1,3-thiazines; N,S-heterocycles; ring expansion; skeletal rearrangement; thiazolidine-4-ones.