Unusual cyclization of N-imidazolyl quinone imines with the formation of thiadiazole ring and its subsequent recyclization

Abstract

2,6-Di-tert-butyl-4-{[2-(2-aryl-2-oxoethylthio)-1H-imidazol-1-yl]imino}cyclohexa-2,5-dien-1-ones under the action of bases give products of the 2,3-dihydroimidazo[2,1-b]thiazol- 3-ol series by subsequent recyclization reaction of the intermediate imidazo[2,1-b][1,3,4]thiadiazoles. The structure of imidazo[2,1-b]thiazol-3-ol is supported by the X-ray diffraction. The features of the cyclization processes of quinone imine derivatives were stimulated by DFT calculations using the wB97XD/6-311++G** method.