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Unusual Cyclization of N-imidazolyl Quinone Imines with the Formation of Thiadiazole Ring and Its Subsequent Recyclization

Mendeleev communications(2022)

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摘要
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.
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Keywords,N -hetaryl quinone imines,recyclization,imidazo[2,b ][1,4]thiadiazoles,b ]thiazoles,DFT calculations
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