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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 |
URI: | https://www.scopus.com/record/display.uri?eid=2-s2.0-85048859223&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=north+caucasus+federal+university&sid=7dd261e865ec559740c571775d0b5e72&sot=afnl&sdt=sisr&cluster=scopubyr%2c%222018%22%2ct&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&ref=%28S+N+H+Arylamination+of+3-Nitropyridine%3a+A+Competitive+Formation+of+2-Arylamino-5-nitropyridines+and+2-Arylamino-5-nitrosopyridines%29&relpos=0&citeCnt=0&searchTerm= http://hdl.handle.net/20.500.12258/2905 |
Appears in Collections: | Статьи, проиндексированные в SCOPUS, WOS |
Files in This Item:
File | Description | Size | Format | |
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scopusresults 238 .pdf Restricted Access | 62.79 kB | Adobe PDF | View/Open | |
WoS 120 .pdf Restricted Access | 75.95 kB | Adobe PDF | View/Open |
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