The First Case of an Aryl Imination Reaction by Direct Nucleophilic Substitution of Hydrogen: Synthesis of 2-arylimino Derivatives for 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines

The oxidative SNH aryl imination of 1-methyl nitro quinolinium salts is described. The first 2-arylimino derivatives of 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines have been synthesized in a one-step reaction (ONSH process) under mild conditions and without preliminary introduction of a leaving gr...

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Κύριοι συγγραφείς:	Pobedinskaya, D. Y., Побединская, Д. Ю., Demidov, O. P., Демидов, О. П., Ermolenko, A. P., Ермоленко, А. П., Avakyan, E. K., Авакян, Е. К., Borovleva, A. A., Боровлева, А. А., Larin, A. N., Ларин, А. Н., Borovlev, I. V., Боровлев, И. В.
Μορφή:	Статья
Γλώσσα:	English
Έκδοση:	John Wiley and Sons Inc 2025
Θέματα:	Heterocyclic imines ONSH process Imination reactions Nucleophilic substitution of hydrogen Quinoline salts
Διαθέσιμο Online:	https://dspace.ncfu.ru/handle/123456789/30368
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spelling	ir-123456789-303682025-04-02T14:07:22Z The First Case of an Aryl Imination Reaction by Direct Nucleophilic Substitution of Hydrogen: Synthesis of 2-arylimino Derivatives for 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines Pobedinskaya, D. Y. Побединская, Д. Ю. Demidov, O. P. Демидов, О. П. Ermolenko, A. P. Ермоленко, А. П. Avakyan, E. K. Авакян, Е. К. Borovleva, A. A. Боровлева, А. А. Larin, A. N. Ларин, А. Н. Borovlev, I. V. Боровлев, И. В. Heterocyclic imines ONSH process Imination reactions Nucleophilic substitution of hydrogen Quinoline salts The oxidative SNH aryl imination of 1-methyl nitro quinolinium salts is described. The first 2-arylimino derivatives of 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines have been synthesized in a one-step reaction (ONSH process) under mild conditions and without preliminary introduction of a leaving group. The resulting products are stable and cannot be obtained via direct interaction of anilines with the corresponding quinolones. The approach found is interesting due to its simplicity of implementation, since the reaction involves the nucleophilic addition of anilines induced by the base, followed by the oxidation of the σH adducts occurring in one pot. This article discusses the synthesis conditions and optimization procedures. We also noted the influence of the position of the nitro group on the reaction yield. A possible reaction mechanism is proposed, supported by the detection of an intermediate product using an NMR experiment. The method's simplicity and retaining the nitro group in the final product offer considerable potential for further structural diversification. 2025-04-02T14:03:05Z 2025-04-02T14:03:05Z 2025 Статья Pobedinskaya D.Y., Demidov O.P., Ermolenko A.P., Avakyan E.K., Borovleva A.A., Larin A.N., Borovlev I.V. The First Case of an Aryl Imination Reaction by Direct Nucleophilic Substitution of Hydrogen: Synthesis of 2-arylimino Derivatives for 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines // ChemistrySelect. - 2025. - 10 (8). - art. no. e202500278. - DOI: 10.1002/slct.202500278 https://dspace.ncfu.ru/handle/123456789/30368 en ChemistrySelect application/pdf application/pdf John Wiley and Sons Inc
institution	СКФУ
collection	Репозиторий
language	English
topic	Heterocyclic imines ONSH process Imination reactions Nucleophilic substitution of hydrogen Quinoline salts
spellingShingle	Heterocyclic imines ONSH process Imination reactions Nucleophilic substitution of hydrogen Quinoline salts Pobedinskaya, D. Y. Побединская, Д. Ю. Demidov, O. P. Демидов, О. П. Ermolenko, A. P. Ермоленко, А. П. Avakyan, E. K. Авакян, Е. К. Borovleva, A. A. Боровлева, А. А. Larin, A. N. Ларин, А. Н. Borovlev, I. V. Боровлев, И. В. The First Case of an Aryl Imination Reaction by Direct Nucleophilic Substitution of Hydrogen: Synthesis of 2-arylimino Derivatives for 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines
description	The oxidative SNH aryl imination of 1-methyl nitro quinolinium salts is described. The first 2-arylimino derivatives of 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines have been synthesized in a one-step reaction (ONSH process) under mild conditions and without preliminary introduction of a leaving group. The resulting products are stable and cannot be obtained via direct interaction of anilines with the corresponding quinolones. The approach found is interesting due to its simplicity of implementation, since the reaction involves the nucleophilic addition of anilines induced by the base, followed by the oxidation of the σH adducts occurring in one pot. This article discusses the synthesis conditions and optimization procedures. We also noted the influence of the position of the nitro group on the reaction yield. A possible reaction mechanism is proposed, supported by the detection of an intermediate product using an NMR experiment. The method's simplicity and retaining the nitro group in the final product offer considerable potential for further structural diversification.
format	Статья
author	Pobedinskaya, D. Y. Побединская, Д. Ю. Demidov, O. P. Демидов, О. П. Ermolenko, A. P. Ермоленко, А. П. Avakyan, E. K. Авакян, Е. К. Borovleva, A. A. Боровлева, А. А. Larin, A. N. Ларин, А. Н. Borovlev, I. V. Боровлев, И. В.
author_facet	Pobedinskaya, D. Y. Побединская, Д. Ю. Demidov, O. P. Демидов, О. П. Ermolenko, A. P. Ермоленко, А. П. Avakyan, E. K. Авакян, Е. К. Borovleva, A. A. Боровлева, А. А. Larin, A. N. Ларин, А. Н. Borovlev, I. V. Боровлев, И. В.
author_sort	Pobedinskaya, D. Y.
title	The First Case of an Aryl Imination Reaction by Direct Nucleophilic Substitution of Hydrogen: Synthesis of 2-arylimino Derivatives for 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines
title_short	The First Case of an Aryl Imination Reaction by Direct Nucleophilic Substitution of Hydrogen: Synthesis of 2-arylimino Derivatives for 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines
title_full	The First Case of an Aryl Imination Reaction by Direct Nucleophilic Substitution of Hydrogen: Synthesis of 2-arylimino Derivatives for 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines
title_fullStr	The First Case of an Aryl Imination Reaction by Direct Nucleophilic Substitution of Hydrogen: Synthesis of 2-arylimino Derivatives for 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines
title_full_unstemmed	The First Case of an Aryl Imination Reaction by Direct Nucleophilic Substitution of Hydrogen: Synthesis of 2-arylimino Derivatives for 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines
title_sort	first case of an aryl imination reaction by direct nucleophilic substitution of hydrogen: synthesis of 2-arylimino derivatives for 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines
publisher	John Wiley and Sons Inc
publishDate	2025
url	https://dspace.ncfu.ru/handle/123456789/30368
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The First Case of an Aryl Imination Reaction by Direct Nucleophilic Substitution of Hydrogen: Synthesis of 2-arylimino Derivatives for 1,2-dihydro-1-methyl-5(6,7,8)-nitroquinolines

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