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S N H Arylamination of 3-Nitropyridine: A Competitive Formation of 2-Arylamino-5-nitropyridines and 2-Arylamino-5-nitrosopyridines

S N H Arylamination of 3-Nitropyridine: A Competitive Formation of 2-Arylamino-5-nitropyridines and 2-Arylamino-5-nitrosopyridines

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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 aromatizat...

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ग्रंथसूची विवरण
मुख्य लेखकों: 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.
स्वरूप: Статья
भाषा:English
प्रकाशित: Georg Thieme Verlag 2018
विषय:
3-nitropyridine
C-H functionalization
Metal-free synthesis
S N H arylamination
ऑनलाइन पहुंच: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=
https://dspace.ncfu.ru/handle/20.500.12258/2905
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spelling oai:10.200.131.19:20.500.12258-29052018-09-12T09:04:27Z S N H Arylamination of 3-Nitropyridine: A Competitive Formation of 2-Arylamino-5-nitropyridines and 2-Arylamino-5-nitrosopyridines 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. 3-nitropyridine C-H functionalization Metal-free synthesis S N H arylamination 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 2018-09-05T13:30:20Z 2018-09-05T13:30:20Z 2018 Статья 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 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 en Synthesis (Germany) application/pdf application/pdf Georg Thieme Verlag
institution СКФУ
collection Репозиторий
language English
topic 3-nitropyridine
C-H functionalization
Metal-free synthesis
S N H arylamination
spellingShingle 3-nitropyridine
C-H functionalization
Metal-free synthesis
S N H arylamination
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.
S N H Arylamination of 3-Nitropyridine: A Competitive Formation of 2-Arylamino-5-nitropyridines and 2-Arylamino-5-nitrosopyridines
description 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
format Статья
author 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.
author_facet 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.
author_sort Borovlev, I. V.
title S N H Arylamination of 3-Nitropyridine: A Competitive Formation of 2-Arylamino-5-nitropyridines and 2-Arylamino-5-nitrosopyridines
title_short S N H Arylamination of 3-Nitropyridine: A Competitive Formation of 2-Arylamino-5-nitropyridines and 2-Arylamino-5-nitrosopyridines
title_full S N H Arylamination of 3-Nitropyridine: A Competitive Formation of 2-Arylamino-5-nitropyridines and 2-Arylamino-5-nitrosopyridines
title_fullStr S N H Arylamination of 3-Nitropyridine: A Competitive Formation of 2-Arylamino-5-nitropyridines and 2-Arylamino-5-nitrosopyridines
title_full_unstemmed S N H Arylamination of 3-Nitropyridine: A Competitive Formation of 2-Arylamino-5-nitropyridines and 2-Arylamino-5-nitrosopyridines
title_sort s n h arylamination of 3-nitropyridine: a competitive formation of 2-arylamino-5-nitropyridines and 2-arylamino-5-nitrosopyridines
publisher Georg Thieme Verlag
publishDate 2018
url 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=
https://dspace.ncfu.ru/handle/20.500.12258/2905
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