Synthesis of a New Class of Chiral Maleimide Derivatives with C2-Symmetry

被引:0
作者
Fu, Liyan [1 ,2 ]
Ji, Baoming [1 ]
Du, Chenxia [2 ]
机构
[1] Luoyang Normal Univ, Coll Chem & Chem Engn, Luoyang 471022, Peoples R China
[2] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
imide; BINOL; organic synthesis; chirality; PROTECTING GROUP; EPOXIDES;
D O I
10.6023/cjoc201703001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Starting from the readily available maleic anhydride and (R)-1,1'-bi-2-naphthol (BINOL), an efficient method for the synthesis of a new class of chiral maleimide derivatives with C-2-symmetry was described, involving Williamson ether synthesis, Suzuki coupling reaction and deprotection reaction by microwave to give 3,4-[(R)-3,3'-diaryl-1,1'-binaphthyl-2,2'-dioxy]-maleimides in 6.2%similar to 16% yields. Moreover, the structures of the target compound and key intermediates were confirmed by H-1 NMR, C-13 NMR, HRMS and IR techniques.
引用
收藏
页码:2685 / 2689
页数:5
相关论文
共 28 条
  • [1] 5-FLUOROURACIL DERIVATIVES .21. A SYNTHESIS OF 5'-O-ACRYLOYL-5-FLUOROURIDINE BY USE OF PARA-METHOXYBENZYL GROUP AS AN N-3-IMIDE PROTECTING GROUP OF 5-FLUOROURIDINE
    AKIYAMA, T
    TAKESUE, Y
    KUMEGAWA, M
    NISHIMOTO, H
    OZAKI, S
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (07) : 2266 - 2269
  • [2] Development of Methods for the Synthesis of Libraries of Substituted Maleimides and α,β-Unsaturated-γ-butyrolactams
    Awuah, Emelia
    Capretta, Alfredo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) : 3122 - 3130
  • [3] 4,5-Diaryl-1H-pyrrole-2-carboxylates as combretastatin A-4/lamellarin T hybrids:: Synthesis and evaluation as anti-mitotic and cytotoxic agents
    Banwell, MG
    Hamel, E
    Hockless, DCR
    Verdier-Pinard, P
    Willis, AC
    Wong, DJ
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (13) : 4627 - 4638
  • [4] Evaluation of alternative approaches for the synthesis of macrocyclic bisindolylmaleimides
    Bartlett, S
    Nelson, A
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (19) : 2874 - 2883
  • [5] 3,3′-Diiodo-BINOL-Fused Maleimides as Chiral Hypervalent Iodine(III) Organocatalysts
    Brenet, Simon
    Berthiol, Florian
    Einhorn, Jacques
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (36) : 8094 - 8096
  • [6] BINOL-Fused Maleimides - A New Class of C2-Symmetric Chiral Imides
    Brenet, Simon
    Baptiste, Benoit
    Philouze, Christian
    Berthiol, Florian
    Einhorn, Jacques
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (06) : 1041 - 1045
  • [7] Double axially chiral bisphosphorylimides as novel Bronsted acids in asymmetric three-component Mannich reaction
    Chen, Ying-Ying
    Jiang, Yi-Jun
    Fan, Yan-Sen
    Sha, Di
    Wang, Qifeng
    Zhang, Guangliang
    Zheng, Liangyu
    Zhang, Suoqin
    [J]. TETRAHEDRON-ASYMMETRY, 2012, 23 (11-12) : 904 - 909
  • [8] Efficient synthesis of a trisubstituted 1,6-naphthyridone from acetonedicarboxylate and regioselective Suzuki arylation
    Chung, JYL
    Cai, CX
    McWilliams, JC
    Reamer, RA
    Dormer, PG
    Cvetovich, RJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (25) : 10342 - 10347
  • [9] Synthesis of substituted bis(heteroaryl)maleimides
    Dubernet, M
    Caubert, V
    Guillard, J
    Viaud-Massuard, MC
    [J]. TETRAHEDRON, 2005, 61 (19) : 4585 - 4593
  • [10] Gao YJ, 2008, CHINESE J ORG CHEM, V28, P8