Transition-Metal-Free Approach to Polysubstituted Furans

被引:24
作者
You, Changming [1 ]
Zhang, Zhenming [1 ]
Tu, Yongliang [1 ]
Tang, Hong [1 ]
Wang, Yuanfeng [1 ]
Long, Da [1 ]
Zhao, Junfeng [1 ,2 ]
机构
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China
[2] Guangzhou Med Univ, Sch Pharmaceut Sci, Guangzhou 511436, Peoples R China
基金
中国国家自然科学基金;
关键词
HIGHLY FUNCTIONALIZED BENZOFURANS; REGIOSELECTIVE SYNTHESIS; H FUNCTIONALIZATION; EFFICIENT; STRATEGY; TANDEM; HYDROXYPHENONES; CONSTRUCTION; CYCLIZATION;
D O I
10.1021/acs.joc.9b03006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and straightforward strategy for the synthesis of 2,3-disubstituted and 2,3,5-trisubstituted furans via a base-promoted domino reaction of beta-keto compounds with vinyl dichlorides is described. This transition-metal-free approach proceeds under operationally simple reaction conditions featuring easily available starting materials, a broad substrate scope, and good functional group tolerance.
引用
收藏
页码:3902 / 3910
页数:9
相关论文
共 46 条
  • [1] An Organocatalytic Approach to 2-Hydroxyalkyl- and 2-Aminoalkyl Furanes
    Albrecht, Lukasz
    Ransborg, Lars Krogager
    Gschwend, Bjorn
    Jorgensen, Karl Anker
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (50) : 17886 - 17893
  • [2] One-Pot Synthesis of Furans Using Base- and Acid-Supported Reagents 'Na2CO3/Al2O3-PPA/SiO2'
    Aoyama, Tadashi
    Nagaoka, Takashi
    Takido, Toshio
    Kodomari, Mitsuo
    [J]. SYNTHESIS-STUTTGART, 2011, (04): : 619 - 625
  • [3] TRANSITION-METAL DIHALOCARBENE COMPLEXES
    BROTHERS, PJ
    ROPER, WR
    [J]. CHEMICAL REVIEWS, 1988, 88 (07) : 1293 - 1326
  • [4] NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONISTS - THE DISCOVERY OF A SERIES OF N-(BIPHENYLYLMETHYL)IMIDAZOLES AS POTENT, ORALLY ACTIVE ANTIHYPERTENSIVES
    CARINI, DJ
    DUNCIA, JV
    ALDRICH, PE
    CHIU, AT
    JOHNSON, AL
    PIERCE, ME
    PRICE, WA
    SANTELLA, JB
    WELLS, GJ
    WEXLER, RR
    WONG, PC
    YOO, SE
    TIMMERMANS, PBMWM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) : 2525 - 2547
  • [5] Synthesis and Metal-Catalyzed Reactions of gem-Dihalovinyl Systems
    Chelucci, Giorgio
    [J]. CHEMICAL REVIEWS, 2012, 112 (03) : 1344 - 1462
  • [6] A facile approach to highly functional trisubstituted furans via intramolecular Wittig reactions
    Chen, Ko-Wei
    Syu, Siang-en
    Jang, Yeong-Jiunn
    Lin, Wenwei
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) : 2098 - 2106
  • [7] Organocatalytic Synthesis of Highly Substituted Furfuryl Alcohols and Amines
    Clark, J. Stephen
    Boyer, Alistair
    Aimon, Anthony
    Garcia, Paloma Engel
    Lindsay, David M.
    Symington, Andrew D. F.
    Danoy, Yves
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (48) : 12128 - 12131
  • [8] Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate
    Coutant, Eloi P.
    Hervin, Vincent
    Gagnot, Glwadys
    Ford, Candice
    Baatallah, Racha
    Janin, Yves L.
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 2853 - 2860
  • [9] Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles
    Dudnik, Alexander S.
    Sromek, Anna W.
    Rubina, Marina
    Kim, Joseph T.
    Kel'in, Alexander V.
    Gevorgyan, Vladimir
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (04) : 1440 - 1452
  • [10] FREY H, 1993, SYNLETT, P905