Copper-Catalyzed Decarboxylative Three-Component Reactions for the Synthesis of Imidazo[1,2-α]pyridines

被引：83

作者：

Palani, Thiruvengadam ^{[1
,2
]}

Park, Kyungho ^{[1
,2
]}

Kumar, Manian Rajesh ^{[1
,2
]}

Jung, Hyun Ming ^{[3
]}

Lee, Sunwoo ^{[1
,2
]}

机构：

[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea

[2] Chonnam Natl Univ, Inst Basic Sci, Kwangju 500757, South Korea

[3] Kumoh Natl Inst Technol, Dept Appl Chem, Gumi 730701, South Korea

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 26期

基金：

新加坡国家研究基金会;

关键词：

Nitrogen heterocycles; Multicomponent reactions; Copper; Alkynes; ALKYNYL CARBOXYLIC-ACIDS; ONE-POT SYNTHESIS; IRIDIUM COMPLEXES; PROPIOLIC ACID; EFFICIENT SYNTHESIS; LIGANDS; DIARYLALKYNES; DERIVATIVES; CYCLIZATION; 2-AMINOPYRIDINES;

D O I：

10.1002/ejoc.201200679

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imidazo[1,2-a]pyridine derivatives were synthesized through multicomponent coupling reactions of 2-aminopyridines, aldehydes, and alkynecarboxylic acids in the presence of 10 mol-% CuI/Cu(OTf)2. Both aryl- and alkyl-substituted alkynecarboxylic acids, including propiolic acid, were good alkyne sources and afforded the desired imidazo[1,2-a]pyridines in good yields through the decarboxylative coupling reactions. Arylalkynecarboxylic acids were synthesized through palladium-catalyzed coupling reactions between aryl iodides and propiolic acid and reacted with 2-aminopyridine and aldehydes, with or without a purification step. In both cases the desired imidazo[1,2-a]pyridines were obtained in good yields. Mechanistic studies suggested that in the case of propiolic acid the decarboxylative addition predominates over terminal alkyne addition.

引用

页码：5038 / 5047

页数：10

共 48 条

[1] Microwave-Assisted, One-Pot Reaction of Pyridines, α-Bromoketones and Ammonium Acetate: An Efficient and Simple Synthesis of Imidazo[1,2-a]-pyridines [J].