Efficient microwave-assisted one-pot three-component synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions

被引：60
|
作者：
Markina, Nataliya A. [1 ]
Chen, Yu [1 ,2 ]
Larock, Richard C. [1 ]
机构：
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
[2] CUNY Queens Coll, Dept Chem & Biochem, Flushing, NY 11367 USA
来源：
TETRAHEDRON | 2013年 / 69卷 / 13期
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
Benzofuran; Sonogashira coupling; Three-component reaction; Microwave; SUBSTITUTED BENZOFURANS; GENERAL-SYNTHESIS; O-ALKYNYLPHENOLS; INDOLES; HETEROCYCLES; ARYL; BOND;
D O I：
10.1016/j.tet.2013.02.003
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient one-pot method for the synthesis of 2,3-disubstituted benzo[b]furans from commercially available 2-iodophenols, terminal acetylenes and aryl iodides has been developed utilizing Sonogashira reaction conditions. After an initial Sonogashira coupling of the 2-iodophenol with the terminal alkyne, cyclization involving the aryl iodide provides the 2,3-disubstituted benzo[b]furan in good to excellent yields. The use of microwave irradiation shortens the reaction times and minimizes the side products. This methodology is especially useful for the construction of libraries of highly substituted benzo[b]furans and their analogues. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2701 / 2713
页数：13
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