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
相关论文
共 50 条
[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 [J].
Ball-Jones, Nicolas R. ;
Badillo, Joseph J. ;
Franz, Annaliese K. .
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 [J].
Cheng, Daojuan ;
Ishihara, Yoshihiro ;
Tan, Bin ;
Barbas, Carlos F., III .
ACS CATALYSIS, 2014, 4 (03) :743-762
[9]   Tetracyclic spirooxindole blockers of hNaV1.7: activity in vitro and in CFA-induced inflammatory pain model [J].
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 .
MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (04) :1825-1836
[10]   Discovery of XEN907, a spirooxindole blocker of NaV1.7 for the treatment of pain [J].
Chowdhury, Sultan ;
Chafeev, Mikhail ;
Liu, Shifeng ;
Sun, Jianyu ;
Raina, Vandna ;
Chui, Ray ;
Young, Wendy ;
Kwan, Rainbow ;
Fu, Jianmin ;
Cadieux, Jay A. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (12) :3676-3681