Homogeneous catalytic aminocarbonylation of nitrogen-containing iodo- heteroaromatics.: Synthesis of N-substituted nicotinamide related compounds

被引：42

作者：

Takacs, Attila ^{[1
]}

Jakab, Balazs ^{[1
]}

Petz, Andrea ^{[1
]}

Kollar, Laszlo ^{[1
]}

机构：

[1] Univ Pecs, Dept Inorgan Chem, H-7624 Pecs, Hungary

来源：

TETRAHEDRON | 2007年 / 63卷 / 41期

基金：

匈牙利科学研究基金会;

关键词：

aminocarbonylation; carbon monoxide; amino acid; palladium; pyridine;

D O I：

10.1016/j.tet.2007.07.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various primary and secondary amines, including amino acid methyl esters, were used as nucleophiles in palladium-catalysed aminocarbonylation of 2-iodopyridine, 3-iodopyridine and iodopyrazine. N-Substituted nicotinamides and 3-pyridyl-glyoxylamides (2-oxo-carboxamide type derivatives) of potential biological importance can be obtained from 3-iodopyridine as a result of simple and double carbon monoxide insertions, respectively. The latter examples can be obtained in synthetically acceptable yields by using elevated carbon monoxide pressure. On the contrary, N-alkyl/ aryl-carboxamides were obtained exclusively in the whole pressure range by using 2-iodopyridine and iodopyrazine. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：10372 / 10378

页数：7

共 16 条

[1] EVIDENCE FOR THE LIGATION OF PALLADIUM(0) COMPLEXES BY ACETATE IONS - CONSEQUENCES ON THE MECHANISM OF THEIR OXIDATIVE ADDITION WITH PHENYL IODIDE AND PHPD(OAC)(PPH(3))(2) AS INTERMEDIATE IN THE HECK REACTION [J].