Efficient synthesis of 7-substituted or 3,7-disubstituted 1H-indazoles

被引：16
作者：
Cottyn, Betty
Vichard, Dominique
Terrier, Francois
Nioche, Pierre
Raman, C. S.
机构：
[1] Univ Versailles, CNRS, UMR 8180, Inst Lavoisier Versailles, F-78035 Versailles, France
[2] Univ Paris 05, F-75270 Paris 06, France
[3] Univ Texas, Sch Med, Dept Biochem & Mol Biol, Houston, TX 77030 USA
来源：
SYNLETT | 2007年 / 08期
关键词：
7-nitro-1H-indazole; indazole; cross-coupling; heterocycles; dihalogenated hetarenes;
D O I：
10.1055/s-2007-977416
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This work reports on the synthesis of the novel indazole scaffolds 7-OTf-1H-indazole (trifluoromethanesulfonic acid 1H-indazol-7-yl ester), 7-iodo-1H-indazole and 3-bromo-7-iodo-1H-indazole. These new compounds are potent building blocks in divergent syntheses of indazoles via palladium cross-coupling reactions.
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收藏
页码：1203 / 1206
页数：4
相关论文
共 40 条
[1]   Cooperative catalyst effects in palladium-mediated cyanation reactions of aryl halides and triflates [J].
Anderson, BA ;
Bell, EC ;
Ginah, FO ;
Harn, NK ;
Pagh, LM ;
Wepsiec, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8224-8228
[2]  
BEHR LC, 1969, PYRAZOLES PYRAZOLINE
[3]   Synthesis and biological evaluation of N-(7-indazolyl)benzenesulfonamide derivatives as potent cell cycle inhibitors [J].
Bouissane, L ;
El Kazzouli, S ;
Léonce, S ;
Pfeiffer, B ;
Rakib, EM ;
Khouili, M ;
Guillaumet, G .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (04) :1078-1088
[4]   New and efficient synthesis of bi- and trisubstituted indazoles [J].
Bouissane, L ;
El Kazzouli, S ;
Léger, JM ;
Jarry, C ;
Rakib, E ;
Khouili, M ;
Guillaumet, G .
TETRAHEDRON, 2005, 61 (34) :8218-8225
[5]   KINETICS, STOICHIOMETRY AND MECHANISM IN BROMINATION OF AROMATIC HETEROCYCLES .3. AQUEOUS BROMINATION OF INDAZOLE [J].
BOULTON, BE ;
COLLER, BAW .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (11) :2343-2347
[6]   Synthesis of new tripodal tri-functionalized hydrotris(indazol-1-yl)borate ligands and X-ray structures of their cyclopentadieneruthenium complexes [J].
Carella, A ;
Vives, G ;
Cox, T ;
Jaud, J ;
Rapenne, G ;
Launay, JP .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2006, (05) :980-987
[7]   Arylated pyridines:: Suzuki reactions of O-substituted 2,6-dihalogenated-3-hydroxypyridines [J].
Chapman, GM ;
Stanforth, SP ;
Tarbit, B ;
Watson, MD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (05) :581-582
[8]   Suzuki-type cross-coupling reaction of 3-iodoindazoles with aryl boronic acids: a general and flexible route to 3-arylindazoles [J].
Collot, V ;
Dallemagne, P ;
Bovy, PR ;
Rault, S .
TETRAHEDRON, 1999, 55 (22) :6917-6922
[9]   First combined selective N- and C-arylations with boronic acids: application to the synthesis of 1,3-diarylindazoles [J].
Collot, V ;
Bovy, PR ;
Rault, S .
TETRAHEDRON LETTERS, 2000, 41 (47) :9053-9057
[10]  
Comins D. L., 1998, ORG SYNTH, V9, P165
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