Syntheses and Characterization of 5-Alkoxy-4-cycloamino-3-halo-5H-furan-2-one

被引：0
|
作者：
Fu, Jianhua [1 ]
Wang, Zhaoyang [1 ]
Hao, Zhifeng [2 ]
Huo, Jingpei [1 ]
机构：
[1] S China Normal Univ, Sch Chem & Environm, Guangzhou 510006, Guangdong, Peoples R China
[2] Guangdong Univ Technol, Fac Chem Engn & Light Ind, Guangzhou 510006, Guangdong, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 31卷 / 09期
关键词：
5-alkoxy-3,4-dihalo-5H-furan-2-one; cyclic secondary amine; Michael addition; tandem reaction; 5-alkoxy-4-cycloamino-3-halo-5H-furan-2-one; synthesis; ENANTIOSELECTIVE SYNTHESIS; GAMMA-BUTENOLIDES; TANDEM REACTION; ALDOL REACTION; ACID; 5-ALKOXY-3,4-DIHALO-5H-FURAN-2-ONE; CATALYSIS; PROGRESS;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Using cyclic secondary amines as nucleophilic reagents, the tandem Michael addition-elimination of 5-alkoxy-3,4-dihalo-5H-furan-2-one in the presence of potassium fluoride gave 17 novel compounds. The chemical structures and absolute configurations of the new compounds were confirmed via rotation, UV-Vis, IR, H-1 NMR, C-13 NMR, MS, elemental analysis and X-ray single crystal diffraction.
引用
收藏
页码：1460 / 1467
页数：8
相关论文
共 37 条
  • [1] Mucohalic acid in Lewis acid catalyzed Mukaiyama aldol reaction:: a concise method for highly functionalized γ-substituted γ-butenolides
    Angell, P
    Zhang, J
    Belmont, D
    Curran, T
    Davidson, JG
    [J]. TETRAHEDRON LETTERS, 2005, 46 (12) : 2029 - 2032
  • [2] An Economical Access to 3,4-Diaryl-2(5H)-furanones and 4-Aryl-6-methyl-2(2H)-pyranones by Pd-Catalyzed Suzuki-Type Arylation of 3-Aryl-4-tosyloxy-2(5H)-furanones and 6-Methyl-4-tosyloxy-2(2H)-pyranones, Respectively
    Bellina, Fabio
    Marchetti, Chiara
    Rossi, Renzo
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (27) : 4685 - 4690
  • [3] Stereoselective radical addition of tertiary amines to (5R)-5-menthyloxy-2[5H]-furanone:: Application to the enantioselective synthesis of (-)-isoretronecanol and (+)-laburnine
    Bertrand, S
    Hoffmann, N
    Pete, JP
    [J]. TETRAHEDRON LETTERS, 1999, 40 (16) : 3173 - 3174
  • [4] Cai Jia-li, 2009, Zhongguo Kangshengsu Zazhi, V34, P454
  • [5] CHEN QH, 1993, ACTA CHIM SINICA, V51, P622
  • [6] Chen QH, 1993, CHINESE J ORG CHEM, V13, P299
  • [7] Direct Asymmetric Allylic Alkylation of Butenolides with Morita-Baylis-Hillman Carbonates
    Cui, Hai-Lei
    Huang, Ji-Rong
    Lei, Jie
    Wang, Zhao-Feng
    Chen, Shi
    Wu, Li
    Chen, Ying-Chun
    [J]. ORGANIC LETTERS, 2010, 12 (04) : 720 - 723
  • [8] Synthesis of surfactants from furfural derived 2[5H]-furanone and fatty amines
    Gassama, Abdoulaye
    Ernenwein, Cedric
    Hoffmann, Norbert
    [J]. GREEN CHEMISTRY, 2010, 12 (05) : 859 - 865
  • [9] Geng Z, 1999, CHINESE J CHEM, V17, P189
  • [10] Synthesis and pharmacological evaluation of a selected library of new potential anti-inflammatory agents bearing the γ-hydroxybutenolide scaffold:: a new class of inhibitors of prostanoid production through the selective modulation of microsomal prostaglandin E synthase-1 expression
    Guerrero, Maria D.
    Aquino, Maurizio
    Bruno, Ines
    Terencio, Maria C.
    Paya, Miguel
    Riccio, Raffaele
    Gomez-Paloma, Luigi
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (09) : 2176 - 2184
1234