Synthesis of fused rings at a pivotal nitrogen:: tandem Heck reactions of N-vinyl-2-iodobenzamides

被引：52
作者：
García, A
Rodríguez, D
Castedo, L
Saá, C
Domínguez, D [1 ]
机构：
[1] Univ Santiago de Compostela, Fac Quim, CSIC, Dept Quim Organ, Santiago De Compostela 15706, Spain
[2] Univ Santiago de Compostela, Fac Quim, CSIC, Unidad Asociada, Santiago De Compostela 15706, Spain
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 10期
关键词：
isoindoles; Heck reactions; enamides; nitrogen heterocycles;
D O I：
10.1016/S0040-4039(01)00077-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short two-step synthesis of the tetracyclic nitrogen heterocycles 2 (isoindoloneindole, isoindoloneisoquinoline and isoindolone[3]benzazepine) is presented. Condensation of the corresponding o-bromoarylamine with acetaldehyde followed by acylation with o-iodobenzoyl chloride affords the key dihalo N-vinylbenzamides 1, which are then cyclized by a tandem Heck reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1903 / 1905
页数：3
相关论文
共 21 条
  • [1] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION
    CABRI, W
    CANDIANI, I
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) : 2 - 7
  • [2] CAMPBELL AL, 1987, SYNTHESIS-STUTTGART, P421
  • [3] FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB
    DE MEIJERE, A
    MEYER, FE
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) : 2379 - 2411
  • [4] THE TOTAL SYNTHESIS OF CHILENINE - NOVEL CONSTRUCTIONS OF CYCLIC ENAMIDES
    FANG, FG
    DANISHEFSKY, SJ
    [J]. TETRAHEDRON LETTERS, 1989, 30 (21) : 2747 - 2750
  • [5] Application of 7-endo, 8-endo and 9-endo radical cyclisations to the synthesis of conformationally constrained amino acids and comparison with the corresponding Heck reactions
    Gibson, SE
    Guillo, N
    Tozer, MJ
    [J]. CHEMICAL COMMUNICATIONS, 1997, (06) : 637 - 638
  • [6] Synthesis of conformationally constrained phenylalanine analogues via 7-, 8- and 9-endo Heck cyclisations
    Gibson, SE
    Guillo, N
    Middleton, RJ
    Thuilliez, A
    Tozer, MJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04): : 447 - 455
  • [7] THE SYNTHESIS OF FUSED RING NITROGEN-HETEROCYCLES VIA REGIOSPECIFIC INTRAMOLECULAR HECK REACTIONS
    GRIGG, R
    SRIDHARAN, V
    STEVENSON, P
    SUKIRTHALINGAM, S
    WORAKUN, T
    [J]. TETRAHEDRON, 1990, 46 (11) : 4003 - 4018
  • [8] Heck R.F., 1991, Comprehensive Organic Synthesis, V4, P833, DOI DOI 10.1016/B978-0-08-052349-1.00110-4
  • [9] Heck R.F., 1985, PALLADIUM REAGENTS O
  • [10] HECK RF, 1982, ORG REACTIONS, V27, P345
123