One-pot highly diastereoselective synthesis of new 2-substituted 8-(spiro-3′-indolino-2′-one)-pyrrolo[3,4-a]pyrrolizine-1,3-diones mediated by azomethine ylide induced by microwave irradiation

被引:27
作者
Azizian, J [1 ]
Asadi, A [1 ]
Jadidi, K [1 ]
机构
[1] Shahid Beheshty Univ, Fac Sci, Dept Chem, Tehran, Iran
关键词
D O I
10.1081/SCC-100105318
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Isatin derivatives react with proline and N-Aryl Maleimides via decarboxylative azomethine ylide formation and subsequent 1,3-dipolar cycloaddition involving an exo-transition state to give new heterocyclic adducts in 71-94% yield.
引用
收藏
页码:2727 / 2733
页数:7
相关论文
共 12 条
  • [1] X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .28. THE IMINIUM ION ROUTE TO AZOMETHINE YLIDES - BACKGROUND AND REACTION OF AMINES WITH BIFUNCTIONAL KETONES
    ARDILL, H
    DORRITY, MJR
    GRIGG, R
    LEONLING, MS
    MALONE, JF
    SRIDHARAN, V
    THIANPATANAGUL, S
    [J]. TETRAHEDRON, 1990, 46 (18) : 6433 - 6448
  • [2] Microwave-induced one-pot synthesis of some new spiro[indoline-3,2′-thiazolidine]-2,4′(1H)-diones and bis[spiro[indoline-3,2′-thiazolidine]2,4′(1H)-diones]
    Azizian, J
    Morady, AV
    Jadidi, K
    Mehrdad, M
    Sarrafi, Y
    [J]. SYNTHETIC COMMUNICATIONS, 2000, 30 (03) : 537 - 542
  • [3] AZIZIAN J, IN PRESS INDIAN J B
  • [4] AZIZIAN J, 2000, SYNTH COMMUN, V27
  • [5] CHIRAL INDUCTION IN CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES DERIVED FROM SECONDARY ALPHA-AMINO-ACIDS BY THE DECARBOXYLATIVE ROUTE
    COULTER, T
    GRIGG, R
    MALONE, JF
    SRIDHARAN, V
    [J]. TETRAHEDRON LETTERS, 1991, 32 (39) : 5417 - 5420
  • [6] X = Y - ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .27. INTRAMOLECULAR CYCLOADDITION REACTIONS OF IMINES OF CYCLIC SECONDARY ALPHA-AMINO ESTERS - DIPOLE AND CYCLOADDITION STEREOCHEMISTRY
    GRIGG, R
    DUFFY, LM
    DORRITY, MJ
    MALONE, JF
    RAJVIROONGIT, S
    THORNTONPETT, M
    [J]. TETRAHEDRON, 1990, 46 (06) : 2213 - 2230
  • [7] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .11. STEREOCHEMISTRY OF 1,3-DIPOLES GENERATED BY THE DECARBOXYLATIVE ROUTE TO AZOMETHINE YLIDES
    GRIGG, R
    SURENDRAKUMAR, S
    THIANPATANAGUL, S
    VIPOND, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (10): : 2693 - 2701
  • [8] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .12. MECHANISM OF FORMATION OF AZOMETHINE YLIDES VIA THE DECARBOXYLATIVE ROUTE FROM ALPHA-AMINO-ACIDS
    GRIGG, R
    IDLE, J
    MCMEEKIN, P
    SURENDRAKUMAR, S
    VIPOND, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (10): : 2703 - 2713
  • [9] Hartmann T., 1995, ALKALOIDS CHEM BIOL, V9
  • [10] JOSHI KC, 1985, HETEROCYCLES, V23, P957