Highly selective 1,3-dipolar cycloadditions of captodative olefins 1-acetylvinyl carboxylates to diverse dipoles

被引：23
|
作者：
Nagarajan, A [1 ]
Zepeda, G [1 ]
Tamariz, J [1 ]
机构：
[1] IPN,ESCUELA NACL CIENCIAS BIOL,DEPT ORGAN CHEM,MEXICO CITY 11340,DF,MEXICO
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 38期
关键词：
D O I：
10.1016/0040-4039(96)01546-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regioselective 1,3-dipolar cycloadditions of captodative 1-acetylvinyl p-nitrobenzoyloxy (1a) with propionitrile oxide, diphenylnitrile imine and diazoalkanes provided the corresponding 5-acetyl- isoxazoles and pyrazoles. Evidence to support the formation of the initial cycloadducts was obtained. The addition of nitrones also proved to be highly regio- and stereoselective. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：6835 / 6838
页数：4
相关论文
共 50 条
  • [31] Understanding the 1,3-Dipolar Cycloadditions of Allenes
    Yu, Song
    Vermeeren, Pascal
    van Dommelen, Kevin
    Bickelhaupt, F. Matthias
    Hamlin, Trevor A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (50) : 11529 - 11539
  • [32] 1,3-DIPOLAR CYCLOADDITIONS OF FULMINIC ACID
    HUISGEN, R
    CHRISTL, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (05) : 456 - &
  • [33] 1,3-dipolar cycloadditions in aqueous media
    Molteni, Giorgio
    HETEROCYCLES, 2006, 68 (10) : 2177 - +
  • [34] 1,3-DIPOLAR CYCLOADDITIONS .24. ADDITION OF NITRONE ESTERS TO MONOACTIVATED OLEFINS
    GREE, R
    TONNARD, F
    CARRIE, R
    TETRAHEDRON, 1976, 32 (06) : 675 - 682
  • [35] π-Face-Selective 1,3-Dipolar Cycloadditions of 3,4-Di-tert-butylthiophene 1-Oxide with 1,3-Dipoles
    Nakayama, Juzo
    Furuya, Tomohiro
    Suzuki, Yasuko
    Hiraiwa, Suguru
    Sugihara, Yoshiaki
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (05) : 1175 - 1183
  • [36] 1,3-Dipolar cycloadditions. Part-XXVIII : Selective 1,3-dipolar cycloadditions of C-aryl-N-phenyl nitrones to arylidene acetones
    Ghosh, Anindita
    Banerji, Avijit
    Banerji, Julie
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2014, 91 (08) : 1393 - 1398
  • [37] 1,3-DIPOLAR CYCLOADDITIONS TO BICYCLIC OLEFINS .3. EFFECTS OF AROMATIC SOLVENTS ON EXO-ENDO PRODUCT RATIOS FOR 1,3-DIPOLAR CYCLOADDITIONS OF NITRILE OXIDES TO NORBORNADIENES
    TANIGUCHI, H
    IMOTO, E
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (08) : 2405 - 2409
  • [38] 1,3-Dipolar cycloadditions to 1,4-quinones
    Wasacz, Colin
    McMahon, Wayne
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [39] MECHANISMS OF 1,3-DIPOLAR CYCLOADDITIONS TO HIGHLY ELECTRON-DEFICIENT DIPOLAROPHILES
    CHANG, YM
    SIMS, J
    HOUK, KN
    TETRAHEDRON LETTERS, 1975, (50) : 4445 - 4448
  • [40] Highly Stereoselective Synthesis of Tricyclic Chromenoisoxazolidines by Intramolecular 1,3-Dipolar Cycloadditions
    Bakthadoss, Manickam
    Murugan, Gandhi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (30) : 5825 - 5830
12345