Synthesis of original thiazoloindolo[3,2-c]quinoline and novel 8-N-substituted-11H-indolo[3,2-c]quinoline derivatives from benzotriazoles.: Part I

被引：19
作者：
Beauchard, A
Chabane, H
Sinbandhit, S
Guenot, P
Thiéry, V
Besson, T
机构：
[1] Univ La Rochelle, CNRS, FRE 2766, Lab Biotechnol & Chim Bioorgan, F-17042 La Rochelle, France
[2] Univ Rennes 1, Ctr Reg Mesures Phys Ouest, F-35042 Rennes, France
来源：
TETRAHEDRON | 2006年 / 62卷 / 08期
关键词：
indoloquinoline; benzotriazoles; fused ring systems; Graebe-Ullmann; microwaves;
D O I：
10.1016/j.tet.2005.09.153
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Synthesis of novel thiazoloindolo[3,2-c]quinoline and 8-substituted-11H-indolo[3,2-c]quinolines was performed via Graebe-Ullmann thermal cyclization from appropriated N-arylated benzotriazoles. 7H-4,7-Diaza-benzo[de]anthracene, a by-product reaction structurally closed to pyridoacridine skeleton was also identified. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1895 / 1903
页数：9
相关论文
共 42 条
[1]  
[Anonymous], [No title captured]
[2]   SYNTHESIS AND REACTIONS OF 4,5-DICHLORO-1,2,3-DITHIAZOLIUM CHLORIDE [J].
APPEL, R ;
JANSSEN, H ;
SIRAY, M ;
KNOCH, F .
CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (04) :1632-1643
[3]  
BESSON T, 2005, HETEROCYCLIC CHEM US, P44
[4]   2-(4-aminophenyl)benzothiazoles: novel agents with selective profiles of in vitro anti-tumour activity [J].
Bradshaw, TD ;
Wrigley, S ;
Shi, DF ;
Schultz, RJ ;
Paull, KD ;
Stevens, MFG .
BRITISH JOURNAL OF CANCER, 1998, 77 (05) :745-752
[5]   Synthesis and cytotoxic activity of thiazolofluorenone derivatives [J].
Chabane, H ;
Pierre, A ;
Leonce, S ;
Pfeiffer, B ;
Renard, P ;
Thiery, V ;
Guillaumet, G ;
Besson, T .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2004, 19 (06) :567-575
[6]   Synthesis and cytotoxic evaluation of novel thiazolocarbazoles. Part II [J].
Chabane, H ;
Lamazzi, C ;
Thiery, V ;
Pierre, A ;
Leonce, S ;
Pfeiffer, B ;
Renard, P ;
Guillaumet, G ;
Besson, T .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2003, 18 (02) :167-174
[7]   Synthesis of novel 2-cyanothiazolocarbazoles analogues of ellipticine [J].
Chabane, H ;
Lamazzi, C ;
Thiéry, V ;
Guillaumet, G ;
Besson, T .
TETRAHEDRON LETTERS, 2002, 43 (14) :2483-2486
[8]   Fischer indole synthesis of the indoloquinoline alkaloid: cryptosanguinolentine [J].
Dhanabal, T ;
Sangeetha, R ;
Mohan, PS .
TETRAHEDRON LETTERS, 2005, 46 (26) :4509-4510
[9]   Focused™ microwave instrumentation from CEM corporation [J].
Ferguson, J. Doug .
MOLECULAR DIVERSITY, 2003, 7 (2-4) :281-286
[10]   Novel 6-substituted benzothiazol-2-yl indolo[1,2-c]quinazolines and benzimidazo[1,2-c]quinazolines [J].
Frère, S ;
Thiéry, V ;
Bailly, C ;
Besson, T .
TETRAHEDRON, 2003, 59 (06) :773-779
12345