SNH Arylamination of 3-Nitropyridine: A Competitive Formation of 2-Arylamino-5-nitropyridines and 2-Arylamino-5-nitrosopyridines

被引：6

作者：

Borovlev, Ivan, V ^{[1
]}

Demidov, Oleg P. ^{[1
]}

Amangasieva, Gulminat A. ^{[1
]}

Avakyan, Elena K. ^{[1
]}

Borovleva, Anastasia A. ^{[1
]}

Pobedinskaya, Diana Yu ^{[1
]}

机构：

[1] North Caucasus Fed Univ, Dept Chem, Pushkin St 1, Stavropol 355009, Russia

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 17期

关键词：

C-H functionalization; S-N(H) arylamination; 3-nitropyridine; metal-free synthesis; NUCLEOPHILIC AROMATIC-SUBSTITUTION; N BOND FORMATION; DIRECT AMINATION; OXIDATIVE ALKYLAMINATION; HYDROGEN; ROUTE; NITROPYRIDINES; AMIDATION; ANILINE; ARENES;

D O I：

10.1055/s-0037-1610173

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 sigma(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.

引用

页码：3520 / 3530

页数：11

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