Direct C-3-Arylations of 1H-Indazoles

被引：48
作者：
Ben-Yahia, Ali [1 ,2 ,3 ]
Naas, Mohammed [2 ,3 ]
El Kazzouli, Said [1 ]
Essassi, El Mokhtar [1 ,2 ]
Guillaumet, Gerald [3 ]
机构：
[1] MAScIR Fdn, Inst Nanomat & Nanotechnol INANO TECH, Rabat 10100, Morocco
[2] Univ Mohammed V Agdal, Lab Chim Organ Heterocycl URAC 21, Rabat, Morocco
[3] Univ Orleans, UMR CNRS 7311, Inst Chim Organ & Analyt, F-45067 Orleans, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 36期
关键词：
Synthetic methods; Nitrogen heterocycles; Homogeneous catalysis; C-C coupling; Cross-coupling; Palladium; N ligands; Ligand effects; CATALYZED DIRECT ARYLATION; EFFICIENT SYNTHESIS; ARYL; HETEROARENES; FUNCTIONALIZATION; 2H-INDAZOLES; DERIVATIVES; INHIBITORS; BROMIDES; DESIGN;
D O I：
10.1002/ejoc.201200860
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first example of intermolecular CH arylation of substituted 1H-indazoles is reported. Various 1-substituted indazoles were used as starting materials, and (hetero)aryl bromides and iodides were investigated as coupling partners. Different reaction conditions were investigated. The best results were obtained using Pd(OAc)2 as catalyst, 1,10-phenanthroline as ligand, K2CO3 as base, and DMA as solvent. The crucial role of the ligand on the CH arylation of substituted 1H-indazoles is highlighted.
引用
收藏
页码：7075 / 7081
页数：7
相关论文
共 45 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[3]   Sonogashira cross-coupling reaction of 3-iodoindazoles with various terminal alkynes: a mild and flexible strategy to design 2-aza tryptamines [J].
Arnautu, A ;
Collot, V ;
Ros, JC ;
Alayrac, C ;
Witulski, B ;
Rault, S .
TETRAHEDRON LETTERS, 2002, 43 (15) :2695-2697
[4]   Design, Synthesis, and Structure-Activity Relationships of 3-Ethynyl-1H-indazoles as Inhibitors of the Phosphatidylintositol 3-Kinase Signaling Pathway [J].
Barile, Elisa ;
De, Surya K. ;
Carlson, Coby B. ;
Chen, Vida ;
Knutzen, Christine ;
Riel-Mehan, Megan ;
Yang, Li ;
Dahl, Russell ;
Chiang, Gary ;
Pellecchia, Maurizio .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (23) :8368-8375
[5]   Catalyst- and Base-Controlled Site-Selective sp2 and sp3 Direct Arylation of 5,7-Dimethyl-2-phenylpyrazolo[1,5-a]pyrimidine Using Aryl Bromides [J].
Bassoude, Ibtissam ;
Berteina-Raboin, Sabine ;
Massip, Stephane ;
Leger, Jean-Michel ;
Jarry, Christian ;
Essassi, El Mokhtar ;
Guillaumet, Gerald .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (13) :2572-2578
[6]   Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C-H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates [J].
Bellina, Fabio ;
Rossi, Renzo .
TETRAHEDRON, 2009, 65 (50) :10269-10310
[7]   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
[8]   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
[9]   Direct Arylation of Imidazo[1,2-a]pyridine at C-3 with Aryl Iodides, Bromides, and Triflates via Copper(I)-Catalyzed C-H Bond Functionalization [J].
Cao, Hua ;
Zhan, Haiying ;
Lin, Yuanguang ;
Lin, Xiulian ;
Du, Zuodong ;
Jiang, Huanfeng .
ORGANIC LETTERS, 2012, 14 (07) :1688-1691
[10]   Heck cross-coupling reaction of 3-iodoindazoles with methyl acrylate: a mild and flexible strategy to design 2-azatryptamines [J].
Collot, V ;
Varlet, D ;
Rault, S .
TETRAHEDRON LETTERS, 2000, 41 (22) :4363-4366
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