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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

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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Hauptverfasser: 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.
Format: Статья
Sprache:English
Veröffentlicht: John Wiley and Sons Inc 2025
Schlagworte:
Heterocyclic imines
ONSH process
Imination reactions
Nucleophilic substitution of hydrogen
Quinoline salts
Online Zugang:https://dspace.ncfu.ru/handle/123456789/30368
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Zusammenfassung: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.

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