Regiospecific synthesis of gem-dinitro derivatives of 2-halogenocycloalka[b]pyridine-3,4-dicarbonitriles

被引：22

作者：

Ershov, Oleg V. ^{[1
]}

Maksimova, Veronika N. ^{[1
]}

Lipin, Konstanin V. ^{[1
]}

Belikov, Mikhail Yu ^{[1
]}

Ievlev, Mikhail Yu ^{[1
]}

Tafeenko, Victor A. ^{[2
]}

Nasakin, Oleg E. ^{[1
]}

机构：

[1] Ulyanov Chuvash State Univ, Cheboksary 428015, Russia

[2] Moscow MV Lomonosov State Univ, Moscow 119991, Russia

来源：

TETRAHEDRON | 2015年 / 71卷 / 39期

基金：

俄罗斯基础研究基金会;

关键词：

Side-chain nitration; gem-Dinitro derivatives; Pyridine; Tetracyanoethylene; 2-Alkylpyridines; Nitric acid; N-OXIDES; RING; PYRIDINIUM; DRUGS; NITROPYRIDINES; PHARMACOLOGY; ALKYLATION; NITRATION; DESIGN; AGENT;

D O I：

10.1016/j.tet.2015.06.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple method for the synthesis of inaccessible gem-dinitro derivatives of pyridine is described. A wide range of 2-halogencycloalka[b]pyridine-3,4-dicarbonitriles are produced by the three-component reaction (ketone, TCNE, hydrohalic acid), side-chain nitration of latter with 60% nitric acid in a solvent-free conditions leads to the formation of gem-dinitro derivatives with high selectivity and without disturbing of other reaction centers. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：7445 / 7450

页数：6

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