Suzuki reaction on pyridinium N-haloheteroarylaminides:: regioselective synthesis of 3,5-disubstituted 2-aminopyrazines

被引：18

作者：

Castillo, Rafael ^{[1
]}

Reyes, M. Jose ^{[1
]}

Izquierdo, M. Luisa ^{[1
]}

Alvarez-Builla, Julio ^{[1
]}

机构：

[1] Univ Alcala de Henares, Dept Quim Organ, Madrid 28871, Spain

来源：

TETRAHEDRON | 2008年 / 64卷 / 07期

关键词：

CROSS-COUPLING REACTIONS; RAPID ANALOG SYNTHESES; RADICAL CYCLIZATION; DERIVATIVES; MIYAURA; AMINIDES; N-(2'-AZINYL)AMINIDES; N-2'-PYRIDYLAMINIDE; CHEMILUMINESCENCE; SNAR;

D O I：

10.1016/j.tet.2007.11.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An extensive study of Suzuki-Miyaura cross-coupling processes on N-pyridinium bromoazinyl aminides has been performed. Mono- and disubstitution on 5- and 3,5-bromo derivatives produced the corresponding aryl derivatives. In the disubstituted compounds regioselective substitution at the 3-position occurred, vicinal to the aminide nitrogen, and this was more evident in pyrazine derivatives. The commonly used strategy involving N-alkylation and reduction of the N-N bond gave rise to a series of 2-alkylamino-3,5-disubstituted-pyrazines. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：1351 / 1370

页数：20

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