Regioselective formation of six- and seven-membered ring by intramolecular Pd-catalyzed amination of N-allyl-anthranilamides

被引:88
作者
Beccalli, EM
Broggini, G
Paladino, G
Penoni, A
Zoni, C
机构
[1] Univ Milan, Fac Farm, Inst Chim Organ A Marchesini, I-20133 Milan, Italy
[2] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy
关键词
D O I
10.1021/jo0495135
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A divergent synthesis of quinazolin-4-ones and 1,4-benzodiazepin-5-ones by Pd(II)-catalyzed intramolecular amination of tosylated N-allyl-anthranilamides is described. Both kinds of products were available in high yields depending on the different reaction conditions.
引用
收藏
页码:5627 / 5630
页数:4
相关论文
共 36 条
  • [1] Regioselectivity on the palladium-catalyzed intramolecular cyclization of indole derivatives
    Abbiati, G
    Beccalli, EM
    Broggini, G
    Zoni, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) : 7625 - 7628
  • [2] Baldessarini R.J., 1985, PHARMACOL BASIS THER, P391
  • [3] Uncommon intramolecular palladium-catalyzed cyclization of indole derivatives
    Beccalli, EM
    Broggini, G
    [J]. TETRAHEDRON LETTERS, 2003, 44 (09) : 1919 - 1921
  • [4] Intramolecular Heck reaction of 2- and 3-iodoindole derivatives for the synthesis of β- and γ-carbolinones
    Beccalli, EM
    Broggini, G
    Marchesini, A
    Rossi, E
    [J]. TETRAHEDRON, 2002, 58 (33) : 6673 - 6678
  • [5] Bekhit AA, 1998, PHARMAZIE, V53, P539
  • [6] Advances and adventures in amination reactions of olefins and alkynes
    Beller, M
    Breindl, C
    Eichberger, M
    Hartung, CG
    Seayad, J
    Thiel, OR
    Tillack, A
    Trauthwein, H
    [J]. SYNLETT, 2002, (10) : 1579 - 1594
  • [7] Catalytic C-H bond functionalization with palladium(II):: Aerobic oxidative annulations of indoles
    Ferreira, EM
    Stoltz, BM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) : 9578 - 9579
  • [8] Fix SR, 2002, ANGEW CHEM INT EDIT, V41, P164, DOI 10.1002/1521-3773(20020104)41:1<164::AID-ANIE164>3.0.CO
  • [9] 2-B
  • [10] Gowan M, 1997, SYNLETT, P1312