Synthesis of polyfunctionalized acrylates via one-pot reactions of arylamines, methyl propiolate, aromatic aldehydes, and active methylene compounds

被引：13
|
作者：
Sun, Yan [1 ]
Sun, Jing [1 ]
Yan, Chao-Guo [1 ]
机构：
[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Peoples R China
来源：
MOLECULAR DIVERSITY | 2012年 / 16卷 / 01期
基金：
中国国家自然科学基金;
关键词：
One-pot reaction; Cyclization; Multicomponent reaction; beta-enamino ester; Electron-deficient alkyne; MCR; QUINOLINE-DMAD ZWITTERION; DIMETHYL ACETYLENEDICARBOXYLATE; DIALKYL ACETYLENEDICARBOXYLATES; 1,4-DIPOLAR CYCLOADDITION; 4-COMPONENT REACTIONS; EFFICIENT SYNTHESIS; CONSTRUCTION; DERIVATIVES;
D O I：
10.1007/s11030-011-9344-z
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
An efficient synthetic method for the densely substituted 3-arylaminoacrylates was successfully developed via the one-pot reaction of arylamines, methyl propiolate, aromatic aldehydes, and active methylene compounds such as pivaloylacetonitrile, 1,3-cyclopentanedione, and 4-hydroxycoumarin. The key step of the reaction was believed to involve the formation of a beta-enamino ester and a sequential Michael addition to the in situ formed arylidene dicarbonyl compound.
引用
收藏
页码：163 / 171
页数：9
相关论文
共 50 条
  • [1] Synthesis of polyfunctionalized acrylates via one-pot reactions of arylamines, methyl propiolate, aromatic aldehydes, and active methylene compounds
    Yan Sun
    Jing Sun
    Chao-Guo Yan
    Molecular Diversity, 2012, 16 : 163 - 171
  • [2] Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes
    Sun, Jing
    Gao, Hong
    Wu, Qun
    Yan, Chao-Guo
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1839 - 1843
  • [3] Synthesis of tetrahydropyrimidin-2-ones via catalyzed one-pot domino reaction of amines, methyl propiolate, aromatic aldehydes, and urea
    Zhang, Li-Li
    Sun, Jing
    Yan, Chao-Guo
    MOLECULAR DIVERSITY, 2014, 18 (01) : 79 - 89
  • [4] Condensation Reactions of Aromatic Aldehydes with Active Methylene Compounds: The Beneficial Sinergy of Alkaline Ionic Liquid in One Pot Synthesis
    Bankar, Swapnil R. R.
    CURRENT ORGANOCATALYSIS, 2022, 9 (03) : 262 - 267
  • [5] Synthesis of Functionalized 2-Aminohydropyridines and 2-Pyridinones via Domino Reactions of Arylamines, Methyl Propiolate, Aromatic Aldehydes, and Substituted Acetonitriles
    Sun, Jing
    Sun, Yan
    Xia, Er-Yan
    Yan, Chao-Guo
    ACS COMBINATORIAL SCIENCE, 2011, 13 (04) : 436 - 441
  • [6] Molecular diversity of acid-catalyzed one-pot reaction of arylamines, methyl propiolate, and isatins
    Hong Gao
    Jing Sun
    Chao-Guo Yan
    Molecular Diversity, 2014, 18 : 511 - 519
  • [7] Molecular diversity of acid-catalyzed one-pot reaction of arylamines, methyl propiolate, and isatins
    Gao, Hong
    Sun, Jing
    Yan, Chao-Guo
    MOLECULAR DIVERSITY, 2014, 18 (03) : 511 - 519
  • [8] CONDENSATION-REACTIONS IN WATER OF ACTIVE METHYLENE-COMPOUNDS WITH ARYLALDEHYDES - ONE-POT SYNTHESIS OF FLAVONOLS
    FRINGUELLI, F
    PANI, G
    PIERMATTI, O
    PIZZO, F
    TETRAHEDRON, 1994, 50 (39) : 11499 - 11508
  • [9] Stereoselective one-pot synthesis of vinylsilanes from aromatic aldehydes
    Kwan, ML
    Yeung, CW
    Breno, KL
    Doxsee, KM
    TETRAHEDRON LETTERS, 2001, 42 (08) : 1411 - 1413
  • [10] One-pot synthesis of novel heterocyclic compounds via tandem reactions
    Huq, C. A. M. A.
    Sivakumar, S.
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2014, 91 (02) : 313 - 317
12345