Efficient synthesis of thiazoloquinazolinone derivatives

被引：54
作者：
Alexandre, FR
Berecibar, A
Wrigglesworth, R
Besson, T
机构：
[1] Univ Rochelle, UFR Sci Fondamentales & Sci Ingenieur, Grp Chim Organ, Lab Genie Prot & Cellulaire,EA3169, F-17042 La Rochelle 1, France
[2] PFIZER, Global Res & Dev, Fresnes Labs, F-94265 Fresnes, France
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 24期
关键词：
thiazoloquinazolinones; quinazolines; 4,5-dichloro-1,2,3-dithiazolium chloride; microwave-assisted chemistry;
D O I：
10.1016/S0040-4039(03)01026-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An original route to the rare 8H-thiazolo[5,4-f]quinazolin-9-one 1 and the novel 7H-thiazolo[4,5-h]quinazolin-6-one 2 is described. Access to the regioisomers was realized by fusion of a thiazole and a quinazoline ring via Appel's salt chemistry. Thermal reactions were carried Out using a focused microwave reactor. reducing the overall time of the multi-step synthesis. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4455 / 4458
页数：4
相关论文
共 27 条
  • [1] Microwave-assisted Niementowski reaction. Back to the roots
    Alexandre, FR
    Berecibar, A
    Besson, T
    [J]. TETRAHEDRON LETTERS, 2002, 43 (21) : 3911 - 3913
  • [2] SYNTHESIS AND REACTIONS OF 4,5-DICHLORO-1,2,3-DITHIAZOLIUM CHLORIDE
    APPEL, R
    JANSSEN, H
    SIRAY, M
    KNOCH, F
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (04): : 1632 - 1643
  • [3] THIAZOLO[5,4-A]ACRIDINES
    BARBE, J
    BOYER, G
    CARIGNANO, I
    ELGUERO, J
    GALY, JP
    MOREL, S
    OUGHEDANI, R
    [J]. TETRAHEDRON LETTERS, 1991, 32 (46) : 6709 - 6710
  • [4] Synthesis and in vitro antitumour evaluation of benzothiazole-2-carbonitrile derivatives
    Bénéteau, V
    Besson, T
    Guillard, J
    Léonce, S
    Pfeiffer, B
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1999, 34 (12) : 1053 - 1060
  • [5] Multistep synthesis of thiazoloquinazolines under microwave irradiation in solution
    Besson, T
    Guillard, J
    Rees, CW
    [J]. TETRAHEDRON LETTERS, 2000, 41 (07) : 1027 - 1030
  • [6] New route to 2-cyanobenzothiazoles via N-arylimino-1,2,3-dithiazoles
    Besson, T
    Dozias, MJ
    Guillard, J
    Rees, CW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (23): : 3925 - 3926
  • [7] SOME CHEMISTRY OF 4,5-DICHLORO-1,2,3-DITHIAZOLIUM CHLORIDE AND ITS DERIVATIVES
    BESSON, T
    REES, CW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (13): : 1659 - 1662
  • [8] Expeditious routes to 4-alkoxyquinazoline-2-carbonitriles and thiocarbamates via N-arylimino-1,2,3-dithiazoles using microwave irradiation
    Besson, T
    Dozias, MJ
    Guillard, J
    Jacquault, P
    Legoy, MD
    Rees, CW
    [J]. TETRAHEDRON, 1998, 54 (23) : 6475 - 6484
  • [9] Synthesis of novel 2-cyanothiazolocarbazoles analogues of ellipticine
    Chabane, H
    Lamazzi, C
    Thiéry, V
    Guillaumet, G
    Besson, T
    [J]. TETRAHEDRON LETTERS, 2002, 43 (14) : 2483 - 2486
  • [10] 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
123