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
相关论文
共 50 条
  • [1] An efficient, microwave-assisted, one-pot synthesis of indoles under Sonogashira conditions
    Chen, Yu
    Markina, Nataliya A.
    Larock, Richard C.
    TETRAHEDRON, 2009, 65 (44) : 8908 - 8915
  • [2] One-pot synthesis of 2,3-disubstituted benzofurans from 2-chlorophenols using palladium-dihydroxyterphenylphosphine catalyst
    Yamaguchi, Miyuki
    Ozawa, Hayato
    Katsumata, Haruka
    Akiyama, Tomoyo
    Manabe, Kei
    TETRAHEDRON LETTERS, 2018, 59 (33) : 3175 - 3178
  • [3] Microwave-assisted one-pot synthesis of 2,3-disubstituted 3H-quinazolin-4-ones
    Liu, JF
    Lee, JY
    Dalton, AM
    Bi, G
    Yu, LB
    Baldino, CM
    McElory, E
    Brown, M
    TETRAHEDRON LETTERS, 2005, 46 (08) : 1241 - 1244
  • [4] Microwave-assisted efficient, one-pot, three-component synthesis of 3,5-disubstituted 1,2,4-oxadiazoles under solvent-free conditions
    Adib, M
    Jahromi, AH
    Tavoosi, N
    Mahdavi, M
    Bijanzadeh, HR
    TETRAHEDRON LETTERS, 2006, 47 (17) : 2965 - 2967
  • [5] Microwave-assisted one-pot three-component synthesis of imine 1,2,3-triazoles
    Souza, Frederico B.
    Pimenta, Daniel C.
    Stefani, Helio A.
    TETRAHEDRON LETTERS, 2016, 57 (14) : 1592 - 1596
  • [6] Three-Component, One-Pot Sequential Synthesis of 1,3-Disubstituted 5-Arylhydantoins
    Olimpieri, Francesca
    Volonterio, Alessandro
    Zanda, Matteo
    SYNLETT, 2008, (19) : 3016 - 3020
  • [7] An Efficient and Regioselective Synthesis of 2,3-Disubstituted 6-Aminoquinoxaline Derivatives Using Alkoxylation and Microwave-assisted Sonogashira Coupling
    Lee, Doohyun
    Seo, Young Ho
    Bae, Jong-Sup
    Lee, Sangkyu
    Lee, Tae Im
    Gong, Young-Dae
    Lee, Taeho
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (08) : 2522 - 2524
  • [8] Microwave-assisted one-pot synthesis of 2,4-disubstituted quinolines under solvent-free conditions
    Yadav, JS
    Reddy, BVS
    Rao, RS
    Naveenkumar, V
    Nagaiah, K
    SYNTHESIS-STUTTGART, 2003, (10): : 1610 - 1614
  • [9] Efficient microwave-assisted diastereoselective synthesis of indole-based 4,5-dihydrofurans via a one-pot, three-component reaction in water
    Robabeh Baharfar
    Razieh Azimi
    Zeinab Asdollahpour
    Environmental Chemistry Letters, 2018, 16 : 677 - 682
  • [10] Efficient microwave-assisted diastereoselective synthesis of indole-based 4,5-dihydrofurans via a one-pot, three-component reaction in water
    Baharfar, Robabeh
    Azimi, Razieh
    Asdollahpour, Zeinab
    ENVIRONMENTAL CHEMISTRY LETTERS, 2018, 16 (02) : 677 - 682
12345