Facile synthesis of 2-substituted benzo[b]furans and indoles by copper-catalyzed intramolecular cyclization of 2-alkynyl phenols and tosylanilines

被引:22
作者
Rong, Zhouting [1 ]
Gao, Kexin [1 ]
Zhou, Lei [1 ]
Lin, Jianyuan [1 ]
Qian, Guoying [1 ]
机构
[1] Zhejiang Wanli Univ, Coll Biol & Environm Sci, Ningbo 315100, Zhejiang, Peoples R China
关键词
ONE-POT SYNTHESIS; BIOACTIVE BENZOFURAN DERIVATIVES; SUBSTITUTED BENZOFURANS; EFFICIENT; ALKALOIDS; FUNCTIONALIZATION; 2-HALOPHENOLS; RELEASE; DOMINO;
D O I
10.1039/c9ra01260e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A catalytic amount of CuCl and Cs2CO3 was employed to synthesize a variety of 2-substituted benzo[b]furans and indoles by an intramolecular cyclization of 2-alkynyl phenols and tosylanilines. This protocol features mild conditions, high yields and broad substrate scope, which makes it a practical method for the synthesis of 2-substituted benzo[b]furans and indoles.
引用
收藏
页码:17975 / 17978
页数:4
相关论文
共 51 条
  • [1] TiCl4-Catalyzed indirect anti-markovnikov hydration of alkynes:: Application to the synthesis of benzo[b]furans
    Ackermann, Lutz
    Kaspar, Ludwig T.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) : 6149 - 6153
  • [2] Aerobic Copper-Catalyzed Organic Reactions
    Allen, Scott E.
    Walvoord, Ryan R.
    Padilla-Salinas, Rosaura
    Kozlowski, Marisa C.
    [J]. CHEMICAL REVIEWS, 2013, 113 (08) : 6234 - 6458
  • [3] A Convenient Synthesis of 2-Arylbenzo[b]furans from Aryl Halides and 2-Halophenols by Catalytic One-Pot Cascade Method
    Bosiak, Mariusz Jan
    [J]. ACS CATALYSIS, 2016, 6 (04): : 2429 - 2434
  • [4] Synthesis and functionalization of Indoles through palladium-catalyzed reactions
    Cacchi, S
    Fabrizi, G
    [J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2873 - 2920
  • [5] Copper catalysis in the construction of indole and benzo[b]furan rings
    Cacchi, Sandro
    Fabrizi, Giancarlo
    Goggiamani, Antonella
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (03) : 641 - 652
  • [6] Impregnated copper or palladium-copper on magnetite as catalysts for the domino and stepwise Sonogashira-cyclization processes: a straightforward synthesis of benzo[b]furans and indoles
    Cano, Rafael
    Yus, Miguel
    Ramon, Diego J.
    [J]. TETRAHEDRON, 2012, 68 (05) : 1393 - 1400
  • [7] Synthesis of benzo[b]furans via CuI-catalyzed ring closure
    Chen, CY
    Dormer, PG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) : 6964 - 6967
  • [8] A novel base-promoted cyclization: synthesis of substituted benzo[b]furans
    Damera, Krishna
    Ke, Bowen
    Wang, Ke
    Dai, Chaofeng
    Wang, Lifang
    Wang, Binghe
    [J]. RSC ADVANCES, 2012, 2 (25): : 9403 - 9405
  • [9] Synthesis of substituted benzofurans via microwave-enhanced catch and release strategy
    De Luca, Lidia
    Giacomelli, Giampaolo
    Nieddu, Giammarlo
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (04): : 517 - 520
  • [10] From Nature to Drug Discovery: The Indole Scaffold as a 'Privileged Structure'
    de Sa Alves, Fernando Rodrigues
    Barreiro, Eliezer J.
    Manssour Fraga, Carlos Alberto
    [J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2009, 9 (07) : 782 - 793