A. A. Kolodina, D. V. Steglenko, E. S. Khodykina, N. I. Gaponenko, M. S. Galkina, O. P. Demidov, A. V. Metelitsa, “Unusual cyclization of <i>N</i>-imidazolyl quinone imines with the formation of thiadiazole ring and its subsequent recyclization”, Mendeleev Commun., 2022, Volume 32, Issue 3,Pages <nobr>386

This article is cited in 1 paper

Communications

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

A. A. Kolodina^a, D. V. Steglenko^a, E. S. Khodykina^a, N. I. Gaponenko^b, M. S. Galkina^a, O. P. Demidov^c, A. V. Metelitsa^a

^a Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don, Russian Federation
^b Information Center for Expertise, Accounting and Analysis of Circulation of Medical Products, Rostov-on-Don, Russian Federation
^c North-Caucasus Federal University, Stavropol, Russian Federation

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.

Keywords: N-hetaryl quinone imines, recyclization, imidazo[2,1-b][1,3,4]thiadiazoles, imidazo[2,1-b]thiazoles, DFT calculations.

Language: English

DOI: 10.1016/j.mencom.2022.05.032

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