Novel series of 8H-quinazolino[4,3-b]quinazolin-8-ones via two Niementowski condensations

被引:87
作者
Alexandre, FR
Berecibar, A
Wrigglesworth, R
Besson, T
机构
[1] Univ La Rochelle, Lab Genie Prot & Cellulaire, EA 3169, Grp Chim Organ,UFR Sci Fondamentales & Sci Ingn, F-17042 La Rochelle 1, France
[2] Pfizer Global Res & Dev, Fresnes Labs, F-94265 Fresnes, France
关键词
nitrogen heterocycles; fused ring systems; microwave-assisted multi-steps synthesis; cyclisation;
D O I
10.1016/S0040-4020(03)00053-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient microwave-assisted multi-step synthesis of 8H-quinazolino[4,3-b]quinazolin-8-one was investigated. The synthesis involved two Niementowski condensations from anthranilic acids. Homogeneous or heterogeneous conditions were studied with the aim to develop convenient syntheses of the desired compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1413 / 1419
页数:7
相关论文
共 39 条
  • [1] ABDELMEGEED MF, 1994, REV ROUM CHIM, V39, P189
  • [2] SYNTHESIS OF SOME NEW CHLORODERIVATIVES OF QUINAZOLINO[4,3-B]QUINAZOLIN-5-ONE AND TETRAZOLO[5,4-C]QUINAZOLINE
    ABDELMEGEED, MF
    YASSIN, SM
    SALEH, MA
    [J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1992, 57 (07) : 1559 - 1564
  • [3] Microwave-assisted Niementowski reaction. Back to the roots
    Alexandre, FR
    Berecibar, A
    Besson, T
    [J]. TETRAHEDRON LETTERS, 2002, 43 (21) : 3911 - 3913
  • [4] Multistep synthesis of thiazoloquinazolines under microwave irradiation in solution
    Besson, T
    Guillard, J
    Rees, CW
    [J]. TETRAHEDRON LETTERS, 2000, 41 (07) : 1027 - 1030
  • [5] CYCLIC AMIDINES .14. DERIVATIVES OF H-7-5,6-A, 12-TRIAZABENZ[A]ANTHRACENE
    BUTLER, K
    PARTRIDGE, MW
    WAITE, JA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1960, (DEC): : 4970 - 4976
  • [6] MICROWAVE-ASSISTED ORGANIC-REACTIONS
    CADDICK, S
    [J]. TETRAHEDRON, 1995, 51 (38) : 10403 - 10432
  • [7] Application of focused microwaves to the scale-up of solvent-free organic reactions
    Cléophax, J
    Liagre, M
    Loupy, A
    Petit, A
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2000, 4 (06) : 498 - 504
  • [8] Efficient modified von Niementowski synthesis of novel derivatives of 5a,14b,15-triazabenzo[a]indeno[1,2-c]anthracen-5-one from indolo[1,2-c]quinazoline
    Domon, L
    Le Coeur, C
    Grelard, A
    Thiéry, V
    Besson, T
    [J]. TETRAHEDRON LETTERS, 2001, 42 (38) : 6671 - 6674
  • [9] QUINAZOLINE DERIVATIVES .1. THE SYNTHESIS OF 4-(4'-DIETHYLAMINO-1'-METHYLBUTYLAMINO)-QUINAZOLINE (SN 11,534) AND THE CORRESPONDING 2-PHENYLQUINAZOLINE (SN 11,535)
    ENDICOTT, MM
    WICK, E
    MERCURY, ML
    SHERRILL, ML
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (07) : 1299 - 1301
  • [10] Microwave-assisted solid-phase synthesis of 5-carboxamido-N-acetyltryptamine derivatives
    Fînaru, A
    Berthault, A
    Besson, T
    Guillaumet, G
    Berteina-Raboin, S
    [J]. ORGANIC LETTERS, 2002, 4 (16) : 2613 - 2615