Intramolecular Cyclization of the ortho-Substituted N-arylquinone Imines under Basic and Thermal Conditions

The S(O,N)-benzyl ethers of N-arylquinone imines undergo cyclization under the action of bases to form products of the benzothiazol, benzoxazole, and benzimidazole series, while under thermal conditions they undergo a non-catalyzed rearrangement to form spiro-cyclohexadiene derivatives of benzazines...

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Главные авторы:	Demidov, O. P., Демидов, О. П.
Формат:	Статья
Язык:	English
Опубликовано:	2023
Темы:	Intramolecular cyclization Ortho-substituted N-arylquinone imines
Online-ссылка:	https://dspace.ncfu.ru/handle/20.500.12258/23486
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spelling	ir-20.500.12258-234862025-02-10T14:39:06Z Intramolecular Cyclization of the ortho-Substituted N-arylquinone Imines under Basic and Thermal Conditions Demidov, O. P. Демидов, О. П. Intramolecular cyclization Ortho-substituted N-arylquinone imines The S(O,N)-benzyl ethers of N-arylquinone imines undergo cyclization under the action of bases to form products of the benzothiazol, benzoxazole, and benzimidazole series, while under thermal conditions they undergo a non-catalyzed rearrangement to form spiro-cyclohexadiene derivatives of benzazines. The benzimidazole, spirobenzothiazine, and spirobenzoxazine structures were supported by the x-ray diffraction method. The possibility of intramolecular photochemical cyclization was investigated; ortho-S(O,N)-benzyl-substituted N-arylquinone imines show high photostability under UV irradiation. The features of the cyclization processes of quinone imine derivatives were revealed by DFT calculations using the wB97XD/6-311++G** method. 2023-05-24T08:23:33Z 2023-05-24T08:23:33Z 2023 Статья Khodykina, E.S., Steglenko, D.V., Vetrova, E.V., Pugachev, A.D., Galkina, M.S., Borodkina, I.G., Lesin, A.V., Demidov, O.P., Metelitsa, A.V., Kolodina, A.A. Intramolecular Cyclization of the ortho-Substituted N-arylquinone Imines under Basic and Thermal Conditions // ChemistrySelect. - 2023. - 8(3), art. no. e202204317. - DOI: 10.1002/slct.202204317 http://hdl.handle.net/20.500.12258/23486 en ChemistrySelect application/pdf application/pdf
institution	СКФУ
collection	Репозиторий
language	English
topic	Intramolecular cyclization Ortho-substituted N-arylquinone imines
spellingShingle	Intramolecular cyclization Ortho-substituted N-arylquinone imines Demidov, O. P. Демидов, О. П. Intramolecular Cyclization of the ortho-Substituted N-arylquinone Imines under Basic and Thermal Conditions
description	The S(O,N)-benzyl ethers of N-arylquinone imines undergo cyclization under the action of bases to form products of the benzothiazol, benzoxazole, and benzimidazole series, while under thermal conditions they undergo a non-catalyzed rearrangement to form spiro-cyclohexadiene derivatives of benzazines. The benzimidazole, spirobenzothiazine, and spirobenzoxazine structures were supported by the x-ray diffraction method. The possibility of intramolecular photochemical cyclization was investigated; ortho-S(O,N)-benzyl-substituted N-arylquinone imines show high photostability under UV irradiation. The features of the cyclization processes of quinone imine derivatives were revealed by DFT calculations using the wB97XD/6-311++G** method.
format	Статья
author	Demidov, O. P. Демидов, О. П.
author_facet	Demidov, O. P. Демидов, О. П.
author_sort	Demidov, O. P.
title	Intramolecular Cyclization of the ortho-Substituted N-arylquinone Imines under Basic and Thermal Conditions
title_short	Intramolecular Cyclization of the ortho-Substituted N-arylquinone Imines under Basic and Thermal Conditions
title_full	Intramolecular Cyclization of the ortho-Substituted N-arylquinone Imines under Basic and Thermal Conditions
title_fullStr	Intramolecular Cyclization of the ortho-Substituted N-arylquinone Imines under Basic and Thermal Conditions
title_full_unstemmed	Intramolecular Cyclization of the ortho-Substituted N-arylquinone Imines under Basic and Thermal Conditions
title_sort	intramolecular cyclization of the ortho-substituted n-arylquinone imines under basic and thermal conditions
publishDate	2023
url	https://dspace.ncfu.ru/handle/20.500.12258/23486
work_keys_str_mv	AT demidovop intramolecularcyclizationoftheorthosubstitutednarylquinoneiminesunderbasicandthermalconditions AT demidovop intramolecularcyclizationoftheorthosubstitutednarylquinoneiminesunderbasicandthermalconditions
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Intramolecular Cyclization of the ortho-Substituted N-arylquinone Imines under Basic and Thermal Conditions

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