Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles

The (2E,2′E)-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis[3-aryl(hetaryl)-2-cyanoprop-2-entioamides] were obtained by treating (E)-3-aryl(hetaryl)-2-cyanoprop-2-entioamides or their [4 + 2] dimerization products, 6-amino-2,4-diaryl-3,5-dicyano-3,4-dihy-dro-2H-thiopyran-3-carbothioamides, with bromine or iod...

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Главные авторы:	Dotsenko, V. V., Доценко, В. В., Aksenov, N. A., Аксенов, Н. А., Aksenova, I. V., Аксенова, И. В.
Формат:	Статья
Язык:	English
Опубликовано:	2023
Online-ссылка:	https://dspace.ncfu.ru/handle/20.500.12258/22260
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spelling	ir-20.500.12258-222602025-02-12T09:41:16Z Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles Dotsenko, V. V. Доценко, В. В. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В. The (2E,2′E)-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis[3-aryl(hetaryl)-2-cyanoprop-2-entioamides] were obtained by treating (E)-3-aryl(hetaryl)-2-cyanoprop-2-entioamides or their [4 + 2] dimerization products, 6-amino-2,4-diaryl-3,5-dicyano-3,4-dihy-dro-2H-thiopyran-3-carbothioamides, with bromine or iodine in DMF. The scope and limitations of the reaction are discussed. Partial ring bromination of starting thioamide was observed only in the case of (E)-2-cyano-3-(4-hydroxy-3-methoxyphenyl) prop-2-enethioamide. When treated with bromine in DMF, 2-cyano-2-cyclopentylideneethanthioamide gives 2,2′-(1,2,4-thiadiazole-3,5-diyl)bis[2-cyclopentylideneacetonitrile] in 69% yield. When 2-imino-7-methoxy-2H-chromene-3-carbothioamide was brominated, 3a,4-dibromo-7-methoxy-3a,4-dihydro-3H-chromeno[2,3-c]isothiazol-3-iminium bromide was isolated instead of the expected 3,3′-(1,2,4-thiadiazole-3,5-diyl)bis(7-methoxy-4a,8a-dihydro-2H-chromene-2-one). The structure of (2E,2′E)-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis{3-[2-(trifluoromethyl)phenyl]acrylonitrile} was confirmed by X-ray studies. Molecular docking was performed in order to find possible protein targets for the prepared new 1,2,4-thiadiazoles. One of the compound, ((2E,2′E)-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis(3-(4-chlorophenyl)acrylonitrile), showed good herbicide safening effect in the experiments with sunflower seedlings. 2023-01-26T14:12:53Z 2023-01-26T14:12:53Z 2023 Статья Krivokolysko, B.S., Dotsenko, V.V., Pakholka, N.A., Dakhno, P.G., Strelkov, V.D., Aksenov, N.A., Aksenova, I.V., Krivokolysko, S.G. Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles // Journal of the Iranian Chemical Society. - 2023. - 20 (3), pp. 609-628. - DOI: 10.1007/s13738-022-02688-4 http://hdl.handle.net/20.500.12258/22260 en Journal of the Iranian Chemical Society application/pdf application/pdf
institution	СКФУ
collection	Репозиторий
language	English
description	The (2E,2′E)-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis[3-aryl(hetaryl)-2-cyanoprop-2-entioamides] were obtained by treating (E)-3-aryl(hetaryl)-2-cyanoprop-2-entioamides or their [4 + 2] dimerization products, 6-amino-2,4-diaryl-3,5-dicyano-3,4-dihy-dro-2H-thiopyran-3-carbothioamides, with bromine or iodine in DMF. The scope and limitations of the reaction are discussed. Partial ring bromination of starting thioamide was observed only in the case of (E)-2-cyano-3-(4-hydroxy-3-methoxyphenyl) prop-2-enethioamide. When treated with bromine in DMF, 2-cyano-2-cyclopentylideneethanthioamide gives 2,2′-(1,2,4-thiadiazole-3,5-diyl)bis[2-cyclopentylideneacetonitrile] in 69% yield. When 2-imino-7-methoxy-2H-chromene-3-carbothioamide was brominated, 3a,4-dibromo-7-methoxy-3a,4-dihydro-3H-chromeno[2,3-c]isothiazol-3-iminium bromide was isolated instead of the expected 3,3′-(1,2,4-thiadiazole-3,5-diyl)bis(7-methoxy-4a,8a-dihydro-2H-chromene-2-one). The structure of (2E,2′E)-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis{3-[2-(trifluoromethyl)phenyl]acrylonitrile} was confirmed by X-ray studies. Molecular docking was performed in order to find possible protein targets for the prepared new 1,2,4-thiadiazoles. One of the compound, ((2E,2′E)-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis(3-(4-chlorophenyl)acrylonitrile), showed good herbicide safening effect in the experiments with sunflower seedlings.
format	Статья
author	Dotsenko, V. V. Доценко, В. В. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В.
spellingShingle	Dotsenko, V. V. Доценко, В. В. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В. Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles
author_facet	Dotsenko, V. V. Доценко, В. В. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В.
author_sort	Dotsenko, V. V.
title	Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles
title_short	Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles
title_full	Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles
title_fullStr	Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles
title_full_unstemmed	Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles
title_sort	bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles
publishDate	2023
url	https://dspace.ncfu.ru/handle/20.500.12258/22260
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Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles

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