Facile preparation of 3-amino-4-(arylamino)-1H-isochromen-1-ones by a new multicomponent reaction

被引：24
作者：
Opatz, T [1 ]
Ferenc, D [1 ]
机构：
[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55138 Mainz, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 05期
关键词：
multicomponent reactions; heterocycles; cyclization; amines; strecker reaction;
D O I：
10.1002/ejoc.200400685
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reactions between 2-formylbenzoic acid, various anilines and HCN result in the formation of 3-amino-4-(arylamino)-1H-isochromen-1-ones in high yield. The mechanism of this three-component condensation involves the intermediate formation of an alpha-aminonitrile and subsequent cyclizationthrough nucleophilic attack of the ortho-carboxylate at the nitrile carbon. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
引用
收藏
页码：817 / 821
页数：5
相关论文
共 20 条
  • [1] SYNTHESIS OF 2-ARYL-3-CYANOPHTHALIMIDINES AND RELATED ANALOGS
    BAUM, JS
    STAVESKI, MM
    [J]. SYNTHETIC COMMUNICATIONS, 1989, 19 (13-14) : 2283 - 2291
  • [2] Bergs H., 1929, Ger. Pat., Patent No. [566,094, 566094]
  • [3] Biginelli P., 1891, BERICHTE DTSCH CHEM, V24, P1317, DOI [DOI 10.1002/CBER.189102401228, 10.1002/cber.189102401228]
  • [4] NEW HYDROGEN-BOND POTENTIALS FOR USE IN DETERMINING ENERGETICALLY FAVORABLE BINDING-SITES ON MOLECULES OF KNOWN STRUCTURE
    BOOBBYER, DNA
    GOODFORD, PJ
    MCWHINNIE, PM
    WADE, RC
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (05) : 1083 - 1094
  • [5] Bucherer HT, 1934, J PRAKTISCHE CHEMIE, V140, P291
  • [6] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
  • [7] 2-U
  • [8] Domling A., 2000, ANGEW CHEM, V112, P3300
  • [9] Hantzsch A., 1882, LIEBIGS ANN CHEM, V215, P1, DOI [10.1002/jlac.18822150102, DOI 10.1002/JLAC.18822150102]
  • [10] Hantzsch A., 1890, BER DTSCH CHEM GES, V23, P1474, DOI [DOI 10.1002/CBER.189002301243, 10.1002/cber.189002301243]
12