An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium

A novel and efficient method for the synthesis of 2-alkylamino and 2-dialkylamino derivatives of N-oxides of 5-, 6-, 7- and 8-nitroquinolines, which can potentially exhibit biological activity, as containing a pharmacophoric quinoline fragment, is described herein. The reactions of 5(6,7,8)-nitroqui...

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Главные авторы:	Larin, A. N., Ларин, А. Н., Avakyan, E. K., Авакян, Е. К., Demidov, O. P., Демидов, О. П., Borovleva, A. A., Боровлева, А. А., Pobedinskaya, D. Y., Побединская, Д. Ю., Ermolenko, A. P., Ермоленко, А. П., Kolosov, S. E., Колосов, С. Е., Borovlev, I. V., Боровлев, И. В.
Formato:	Статья
Idioma:	English
Publicado:	John Wiley and Sons Inc 2025
Темы:	Alkylamination ONSH C−H activation Nitroquinoline N-oxides Nucleophilic substitution of hydrogen
Acceso en liña:	https://dspace.ncfu.ru/handle/123456789/29634
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spelling	ir-123456789-296342025-02-06T12:22:50Z An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium Larin, A. N. Ларин, А. Н. Avakyan, E. K. Авакян, Е. К. Demidov, O. P. Демидов, О. П. Borovleva, A. A. Боровлева, А. А. Pobedinskaya, D. Y. Побединская, Д. Ю. Ermolenko, A. P. Ермоленко, А. П. Kolosov, S. E. Колосов, С. Е. Borovlev, I. V. Боровлев, И. В. Alkylamination ONSH C−H activation Nitroquinoline N-oxides Nucleophilic substitution of hydrogen A novel and efficient method for the synthesis of 2-alkylamino and 2-dialkylamino derivatives of N-oxides of 5-, 6-, 7- and 8-nitroquinolines, which can potentially exhibit biological activity, as containing a pharmacophoric quinoline fragment, is described herein. The reactions of 5(6,7,8)-nitroquinoline N-oxides with various primary or secondary amines in the presence of potassium ferricyanide at in aqueous dioxane medium afforded the corresponding secondary and tertiary amines in moderate to excellent yields. This reaction is the first example of a Chichibabin reaction leading to the formation of 2-alkylaminoquinoline derivatives at position 2 under mild conditions. A study of the antibacterial activity of some products was carried out. 2025-02-06T12:16:20Z 2025-02-06T12:16:20Z 2025 Статья Larin, A.N., Avakyan, E.K., Demidov, O.P., Borovleva, A.A., Zubenko, A.A., Pobedinskaya, D.Y., Ermolenko, A.P., Kolosov, S.E., Borovlev, I.V. An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium // European Journal of Organic Chemistry. - 2025. - 28 (3). - статья № e202401060. - DOI: 10.1002/ejoc.202401060 https://dspace.ncfu.ru/handle/123456789/29634 en European Journal of Organic Chemistry application/pdf application/pdf John Wiley and Sons Inc
institution	СКФУ
collection	Репозиторий
language	English
topic	Alkylamination ONSH C−H activation Nitroquinoline N-oxides Nucleophilic substitution of hydrogen
spellingShingle	Alkylamination ONSH C−H activation Nitroquinoline N-oxides Nucleophilic substitution of hydrogen Larin, A. N. Ларин, А. Н. Avakyan, E. K. Авакян, Е. К. Demidov, O. P. Демидов, О. П. Borovleva, A. A. Боровлева, А. А. Pobedinskaya, D. Y. Побединская, Д. Ю. Ermolenko, A. P. Ермоленко, А. П. Kolosov, S. E. Колосов, С. Е. Borovlev, I. V. Боровлев, И. В. An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium
description	A novel and efficient method for the synthesis of 2-alkylamino and 2-dialkylamino derivatives of N-oxides of 5-, 6-, 7- and 8-nitroquinolines, which can potentially exhibit biological activity, as containing a pharmacophoric quinoline fragment, is described herein. The reactions of 5(6,7,8)-nitroquinoline N-oxides with various primary or secondary amines in the presence of potassium ferricyanide at in aqueous dioxane medium afforded the corresponding secondary and tertiary amines in moderate to excellent yields. This reaction is the first example of a Chichibabin reaction leading to the formation of 2-alkylaminoquinoline derivatives at position 2 under mild conditions. A study of the antibacterial activity of some products was carried out.
format	Статья
author	Larin, A. N. Ларин, А. Н. Avakyan, E. K. Авакян, Е. К. Demidov, O. P. Демидов, О. П. Borovleva, A. A. Боровлева, А. А. Pobedinskaya, D. Y. Побединская, Д. Ю. Ermolenko, A. P. Ермоленко, А. П. Kolosov, S. E. Колосов, С. Е. Borovlev, I. V. Боровлев, И. В.
author_facet	Larin, A. N. Ларин, А. Н. Avakyan, E. K. Авакян, Е. К. Demidov, O. P. Демидов, О. П. Borovleva, A. A. Боровлева, А. А. Pobedinskaya, D. Y. Побединская, Д. Ю. Ermolenko, A. P. Ермоленко, А. П. Kolosov, S. E. Колосов, С. Е. Borovlev, I. V. Боровлев, И. В.
author_sort	Larin, A. N.
title	An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium
title_short	An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium
title_full	An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium
title_fullStr	An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium
title_full_unstemmed	An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium
title_sort	oxidative snh alkylamination of 5(6,7,8)-nitroquinoline n-oxides in aqueous dioxane medium
publisher	John Wiley and Sons Inc
publishDate	2025
url	https://dspace.ncfu.ru/handle/123456789/29634
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An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium

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