A facile base-promoted domino Michael/O-alkylation reaction for the construction of succinimide-substituted 3(2H)-furanones

被引:0
作者
Wang, Wu [1 ]
Liang, Guojuan [1 ]
Bai, Yan [1 ]
Bai, Lijuan [1 ]
Zhou, Hui [1 ]
Yu, Yu [1 ]
Zhou, Jing [1 ]
机构
[1] Chongqing Med Univ, Sch Pharmaceut Sci, Chongqing Res Ctr Pharmaceut Engn, Chongqing Key Lab Biochem & Mol Pharmacol, Chongqing 400016, Peoples R China
基金
中国国家自然科学基金;
关键词
Succinimide-substituted 3(2H)-furanones; Michael/O-alkylation; domino reaction; maleimides; gamma-halogenated-beta-ketoesters; REACTIONS ASYMMETRIC-SYNTHESIS; TETRONIC ACID-DERIVATIVES; ENANTIOSELECTIVE SYNTHESIS; ALDOL REACTION; MALEIMIDES; CYCLOADDITION;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel base-promoted domino Michael/O-alkylation reaction of maleimides with gamma-halogenated-beta-ketoesters is described. A variety of new succinimide-substituted 3(2H)-furanones were obtained in excellent yields (up to 96%) under simple and mild conditions. The structure of the new compound 3a was determined by single crystal X-ray analysis and a reaction pathway is proposed. [GRAPHICS] .
引用
收藏
页码:236 / 248
页数:13
相关论文
共 36 条
[1]   FURAN-3(2H)-ONES BY TANDEM PHOTO-OXIDATION INTRAMOLECULAR MICHAEL ADDITION [J].
ANTONIOLETTI, R ;
BONADIES, F ;
PRENCIPE, T ;
SCETTRI, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (13) :850-851
[2]   Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones [J].
Bunnelle, Eric M. ;
Smith, Cameron R. ;
Lee, Sharon K. ;
Singaram, Surendra W. ;
Rhodes, Allison J. ;
Sarpong, Richmond .
TETRAHEDRON, 2008, 64 (29) :7008-7014
[3]   Synthesis of 4-iodo-3-furanones utilizing electrophile-induced tandem cyclization/1,2-migration reactions [J].
Crone, Benedikt ;
Kirsch, Stefan F. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5435-5438
[4]  
Diez E. S., 2016, ORG LETT, V18, P1270
[5]   From the Feist-Benary Reaction to Organocatalytic Domino Michael-Alkylation Reactions: Asymmetric Synthesis of 3(2H)-Furanones [J].
Dou, Xiaowei ;
Han, Xiaoyu ;
Lu, Yixin .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (01) :85-89
[6]   Cationic Gold(I)-Catalyzed Intramolecular Cyclization of γ-Hydroxyalkynones into 3(2H)-Furanones [J].
Egi, Masahiro ;
Azechi, Kenji ;
Saneto, Moriaki ;
Shimizu, Kaori ;
Akai, Shuji .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (06) :2123-2126
[7]   Highly enantioselective direct vinylogous Michael addition of γ-substituted deconjugated butenolides to maleimides catalyzed by chiral squaramides [J].
Guo, Yun-Long ;
Jia, Li-Na ;
Peng, Lin ;
Qi, Liang-Wen ;
Zhou, Jing ;
Tian, Fang ;
Xu, Xiao-Ying ;
Wang, Li-Xin .
RSC ADVANCES, 2013, 3 (38) :16973-16976
[8]   A Recyclable, Immobilized Analogue of Benzotetramisole for Catalytic Enantioselective Domino Michael Addition/Cyclization Reactions in Batch and Flow [J].
Izquierdo, Javier ;
Pericas, Miguel A. .
ACS CATALYSIS, 2016, 6 (01) :348-356
[9]   SYNTHESIS AND CONFIGURATIONAL ASSIGNMENT OF GEIPARVARIN - A NOVEL ANTI-TUMOR AGENT [J].
JERRIS, PJ ;
SMITH, AB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (03) :577-585
[10]   A tandem Mannich addition-palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones [J].
John, Jubi ;
Tarcoveanu, Eliza ;
Jones, Peter G. ;
Hopf, Henning .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 :1462-1470