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Title: S N H arylamination of 3-nitropyridine: a competitive formation of 2-arylamino-5-nitropyridines and 2-arylamino-5-nitrosopyridines
Authors: Borovlev, I. V.
Боровлев, И. В.
Demidov, O. P.
Демидов, О. П.
Amangasieva, G. A.
Амангазиева, Г. А.
Avakyan, E. K.
Авакян, Е. К.
Borovleva, A. A.
Боровлева, А. А.
Pobedinskaya, D. Y.
Побединская, Д. Ю.
Keywords: 3-nitropyridine;C-H functionalization;Metal-free synthesis;S N H arylamination
Issue Date: 2018
Publisher: Georg Thieme Verlag
Citation: Borovlev, I.V., Demidov, O.P., Amangasieva, G.A., Avakyan, E.K., Borovleva, A.A., Pobedinskaya, D.Y. S N H Arylamination of 3-Nitropyridine: A Competitive Formation of 2-Arylamino-5-nitropyridines and 2-Arylamino-5-nitrosopyridines // Synthesis (Germany). - 2018. - Volume 50. - Issue 17. - Pages 3520-3530
Series/Report no.: Synthesis (Germany)
Abstract: Arylamination of 3-nitropyridine via the nucleophilic substitution of hydrogen leads to a mixture of 2-arylamino-5-nitropyridines and novel 2-arylamino-5-nitrosopyridines, with the latter as the major product. The proposed mechanism includes the formation of σ H -adducts and their further aromatization proceeding either through an oxidative pathway or intramolecular Red/Ox pathway of the S N H reaction. Moreover, we have shown that nitroso compounds can be selectively oxidized with m -chloroperbenzoic acid to give the corresponding nitro derivatives or their N -oxides, depending on the reaction temperature and the amount of oxidant
Appears in Collections:Статьи, проиндексированные в SCOPUS, WOS

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