Diversified Synthesis of Furans by Coupling between Enols/1,3-Dicarbonyl Compounds and Nitroolefins: Direct Access to Dioxa[5]helicenes

被引：39
作者：
Ghosh, Monoranjan [1 ]
Santra, Sougata [1 ]
Mondal, Pallab [1 ]
Kundu, Dhiman [1 ]
Hajra, Alakananda [1 ]
机构：
[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2015年 / 10卷 / 11期
关键词：
denitration; furans; helicenes; heterocycles; synthetic methods; BAYLIS-HILLMAN ACETATES; POLYSUBSTITUTED FURANS; 1,3-DICARBONYL COMPOUNDS; REGIOSELECTIVE SYNTHESIS; REGIOSPECIFIC SYNTHESIS; ANNULATION; KETONES; NITROALKANES; BENZOFURANS; CYCLIZATION;
D O I：
10.1002/asia.201500710
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A versatile method for the diversified synthesis of furans and arenofurans has been developed that proceeds through K2CO3-promoted cyclization between enols/1,3-dicarbonyl compounds and nitroolefins at reflux in EtOH. This facile method has been successfully employed in the synthesis of benzotrifuran derivatives, which are useful hole-transporting materials. This procedure also provides direct access to dioxa[5]helicenes. This reaction offers a broad substrate scope, uses an inexpensive base and environmentally benign solvent, and is operationally simple.
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收藏
页码：2525 / 2536
页数：12
相关论文
共 86 条
  • [1] SYNTHESIS OF SUBSTITUTED 2,3,5,6-TETRAARYLBENZO[1,2-B-5,4-B']DIFURANS
    ABDULAZIZ, M
    AUPING, JV
    MEADOR, MA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) : 1303 - 1308
  • [2] Adachi C., 2004, ORGANIC LIGHT EMITTI, P43
  • [3] Orthogonal selectivity with cinnamic acids in 3-substituted benzofuran synthesis through C-H olefination of phenols
    Agasti, Soumitra
    Sharma, Upendra
    Naveen, Togati
    Maiti, Debabrata
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (25) : 5375 - 5378
  • [4] INTERMEDIATES IN THE PAAL-KNORR SYNTHESIS OF FURANS
    AMARNATH, V
    AMARNATH, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (02) : 301 - 307
  • [5] [Anonymous], 2013, ANGEW CHEM
  • [6] [Anonymous], 2008, RJK TAYLOR
  • [7] An Efficient Friedel-Crafts/Oxa-Michael/Aromatic Annulation: Rapid Access to Substituted Naphtho[2,1-b]furan, Naphtho[1,2-b]furan, and Benzofuran Derivatives
    Anwar, Shaik
    Huang, Wan-Yun
    Chen, Chih-Hao
    Cheng, You-Song
    Chen, Kwunmin
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (13) : 4344 - 4351
  • [8] Synthetic, crystallographic, computational, and biological studies of 1,4-difluorobenzo[c]phenanthrene and its metabolites
    Bae, Suyeal
    Mah, Heduck
    Chaturvedi, Surendrakumar
    Jeknic, Tamara Musafia
    Baird, William M.
    Katz, Amy K.
    Carrell, H. L.
    Glusker, Jenny P.
    Okazaki, Takao
    Laali, Kenneth K.
    Zajc, Barbara
    Lakshman, Mahesh K.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (20) : 7625 - 7633
  • [9] Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results
    Ballini, R
    Bosica, G
    Fiorini, D
    Palmieri, A
    Petrini, M
    [J]. CHEMICAL REVIEWS, 2005, 105 (03) : 933 - 971
  • [10] Relationship between the structure and the DNA binding properties of diazoniapolycyclic duplex- and Triplex-DNA binders: Efficiency, selectivity, and binding mode
    Basili, Serena
    Bergen, Anna
    Dall'Acqua, Francesco
    Faccio, Anita
    Granzhan, Anton
    Ihmels, Heiko
    Moro, Stefano
    Viola, Giampietro
    [J]. BIOCHEMISTRY, 2007, 46 (44) : 12721 - 12736
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