A General and Efficient Method to Access Tetracyclic Spirooxindole Derivatives

被引:15
作者
El Bouakher, Abderrahman [1 ]
Massip, Stephane [2 ]
Jarry, Christian [2 ]
Troin, Yves [3 ,4 ]
Abrunhosa-Thomas, Isabelle [3 ,4 ]
Guillaumet, Gerald [1 ]
机构
[1] Univ Orleans, CNRS, UMR 7311, Inst Chim Organ & Analyt, F-45067 Orleans, France
[2] Univ Bordeaux Segalen, CNRS, FRE 3396, F-33000 Bordeaux, France
[3] Clermont Univ, ENSCCF, ICCF, F-63000 Clermont Ferrand, France
[4] ICCF, CNRS, UMR 6296, F-63171 Aubiere, France
关键词
Anionic condensation; Reduction; Cyclization; Selective deprotection; Tetracyclic spirooxindole; Spiro compounds; REVERSE-TRANSCRIPTASE INHIBITORS; ENANTIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATIONS; STRESS METABOLITES; METALATION; OXINDOLES; BIOSYNTHESIS; PHYTOALEXIN; CARBOLINES; FRAGMENT;
D O I
10.1002/ejoc.201403292
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, simple, and convenient synthetic procedure for the synthesis of tetracyclic spirooxindole derivatives, starting from N-protected isatins and 2-fluoropyridine, was success-fully developed. It enables the facile formation of a new class of spirooxindoles in which the oxindole core is fused with various heterocycles at the C-3 position.
引用
收藏
页码:556 / 569
页数:14
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  • [1] ANNAKA M, 1994, HETEROCYCLES, V39, P251
  • [2] [Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1103/PHYSREVLETT.112.077206
  • [3] Strategies for the enantioselective synthesis of spirooxindoles
    Ball-Jones, Nicolas R.
    Badillo, Joseph J.
    Franz, Annaliese K.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) : 5165 - 5181
  • [4] BENARAB A, 1993, HETEROCYCLES, V36, P2327
  • [5] Cadieux J. J., 2008, [No title captured], Patent No. [WO2008046049 (Al), 2008046049]
  • [6] Chafeev M., 2006, [No title captured], Patent No. [2006110917, 2006110917A2]
  • [7] Chafeev M., 2008, [No title captured], Patent No. [2008060789, 2008060789A2]
  • [8] Organocatalytic Asymmetric Assembly Reactions: Synthesis of Spirooxindoles via Organocascade Strategies
    Cheng, Daojuan
    Ishihara, Yoshihiro
    Tan, Bin
    Barbas, Carlos F., III
    [J]. ACS CATALYSIS, 2014, 4 (03): : 743 - 762
  • [9] Tetracyclic spirooxindole blockers of hNaV1.7: activity in vitro and in CFA-induced inflammatory pain model
    Chowdhury, Sultan
    Liu, Shifeng
    Cadieux, Jay A.
    Hsieh, Tom
    Chafeev, Mikhail
    Sun, Shaoyi
    Jia, Qi
    Sun, Jianyu
    Wood, Mark
    Langille, Jonathan
    Sviridov, Serguei
    Fu, Jianmin
    Zhang, Zaihui
    Chui, Ray
    Wang, Audrey
    Cheng, Xing
    Zhong, Jing
    Hossain, Sazzad
    Khakh, Kuldip
    Rajlic, Ivana
    Verschoof, Henry
    Kwan, Rainbow
    Young, Wendy
    [J]. MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (04) : 1825 - 1836
  • [10] Discovery of XEN907, a spirooxindole blocker of NaV1.7 for the treatment of pain
    Chowdhury, Sultan
    Chafeev, Mikhail
    Liu, Shifeng
    Sun, Jianyu
    Raina, Vandna
    Chui, Ray
    Young, Wendy
    Kwan, Rainbow
    Fu, Jianmin
    Cadieux, Jay A.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (12) : 3676 - 3681