Hypervalent Iodine Mediated Oxidative Cyclization of o-Hydroxystilbenes into Benzo- and Naphthofurans

被引：68
作者：
Singh, Fateh V. [1 ]
Wirth, Thomas [1 ]
机构：
[1] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, S Glam, Wales
来源：
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 08期
关键词：
benzofurans; cyclization; hypervalent iodine reagents; naphthofurans; stilbenes; PLANT HERITIERA-LITTORALIS; 2,3-DISUBSTITUTED BENZOFURANS; EFFICIENT SYNTHESIS; COUPLING REACTIONS; MANGROVE PLANTS; DERIVATIVES; CHEMISTRY; KETONES; PHENOLS; ANALOGS;
D O I：
10.1055/s-0031-1290588
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new and convenient metal-free cyclization of ortho-hydroxystilbenes into 2-arylbenzofurans and 2-arylnaphthofurans mediated by hypervalent iodine reagents is described. The cyclization products are isolated in good to excellent yields using stoichiometric (diacetoxyiodo)benzene in acetonitrile.
引用
收藏
页码：1171 / 1177
页数：7
相关论文
共 71 条
  • [1] The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans
    Anderson, Kevin W.
    Ikawa, Takashi
    Tundel, Rachel E.
    Buchwald, Stephen L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) : 10694 - 10695
  • [2] [Anonymous], 2003, TOPICS CURRENT CHEM
  • [3] Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues
    Aslam, SN
    Stevenson, PC
    Phythian, SJ
    Veitch, NC
    Hall, DR
    [J]. TETRAHEDRON, 2006, 62 (17) : 4214 - 4226
  • [4] INVESTIGATIONS ON BENZOFURANS .60. ORIENTATION OF ALKALINE-DEGRADATION OF 3-AROYL-2-ETHYLBENZOFURANS ACCORDING TO NATURE OF AROYL GROUP
    ASTOIN, J
    DEMERSEMAN, P
    RIVERON, A
    ROYER, R
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (05) : 867 - 869
  • [5] NATURALLY OCCURRING TERPENE DERIVATIVES .80. SOME CONSTITUENTS OF GENUS CHROMOLAENA
    BOHLMANN, F
    ZDERO, C
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (02): : 487 - 490
  • [6] Novel lactonization with phenonium ion participation induced by hypervalent iodine reagents
    Boye, AC
    Meyer, D
    Ingison, CK
    French, AN
    Wirth, T
    [J]. ORGANIC LETTERS, 2003, 5 (12) : 2157 - 2159
  • [7] Braga de Oliveira A., 1978, TETRAHEDRON LETT, V19, P2653
  • [8] On-water chemistry:: Copper-catalyzed straightforward synthesis of benzo[b]furan derivatives in neat water
    Carril, M
    SanMartin, R
    Tellitu, I
    Domínguez, E
    [J]. ORGANIC LETTERS, 2006, 8 (07) : 1467 - 1470
  • [9] Iron-catalyzed Sonogashira reactions
    Carril, Monica
    Correa, Arkaitz
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) : 4862 - 4865
  • [10] Syntheses of indoles via a palladium-catalyzed annulation between iodoanilines and ketones
    Chen, CY
    Lieberman, DR
    Larsen, RD
    Verhoeven, TR
    Reider, PJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) : 2676 - 2677
12345678