Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization

被引:30
作者
Sofia Santos, A. [1 ]
Mortinho, Ana C. [1 ]
Marques, M. Manuel B. [1 ]
机构
[1] Univ Nova Lisboa, Dept Quim, LAQV REQUIMTE, Fac Ciencias & Tecnol, Campus Caparica, P-2829516 Caparica, Portugal
关键词
azaindole; metal-catalyzed; heterocycles; cross-coupling reactions; ONE-POT SYNTHESIS; C-H ACTIVATION; 7-AZAINDOLES; INDOLES; HETEROANNULATION; DESIGN; AMINOPYRIDINES; 4-AZAINDOLES; ANNULATION; INHIBITORS;
D O I
10.3390/molecules23102673
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Azaindoles are rare in nature but extremely attractive for drug discovery programs. Azaindoles can be obtained by diverse methods, including those involving metal-catalyzed reactions. This important core has been fascinating the scientific community due to their challenging synthesis and relevant bioactivity. This paper highlights the diverse synthetic methodologies developed to date involving metal-catalyzed reaction to attain azaindoles and its functionalization.
引用
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页数:16
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共 46 条
[1]  
Antonio A., 1992, TETRAHEDRON LETT, V33, P3915
[2]   Heterocyclic enaminones:: Photochemical synthesis of 6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indol-9-ones [J].
Blache, Y ;
Sinibaldi-Troin, ME ;
Hichour, M ;
Benezech, V ;
Chavignon, O ;
Gramain, JC ;
Teulade, JC ;
Chapat, JP .
TETRAHEDRON, 1999, 55 (07) :1959-1970
[3]   Palladium-Catalyzed Selective Dehydrogenative Cross-Couplings of Heteroarenes [J].
Bugaut, Xavier ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7479-7481
[4]   The aminopalladation-reductive elimination process as a tool for the solution-phase synthesis of 2,3-disubstituted azaindole libraries [J].
Cacchi, S ;
Fabrizi, G ;
Parisi, LM .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (04) :510-512
[5]   Palladium-catalyzed functionalization of 5-and 7-azaindoles [J].
Chi, SM ;
Choi, JK ;
Yum, EK ;
Chi, DY .
TETRAHEDRON LETTERS, 2000, 41 (06) :919-922
[6]   Chemoselective Aliphatic C-H Bond Oxidation Enabled by Polarity Reversal [J].
Dantignana, Valeria ;
Milan, Michela ;
Cusso, Olaf ;
Company, Anna ;
Bietti, Massimo ;
Costas, Miquel .
ACS CENTRAL SCIENCE, 2017, 3 (12) :1350-1358
[7]   Metal-free nitrative cyclization of N-aryl imines with tert-butyl nitrite: dehydrogenative access to 3-nitroindoles [J].
Deng, Guo-Bo ;
Zhang, Jia-Ling ;
Liu, Yan-Yun ;
Liu, Bang ;
Yang, Xu-Heng ;
Li, Jin-Heng .
CHEMICAL COMMUNICATIONS, 2015, 51 (10) :1886-1888
[8]   TRANSITION-METAL-CATALYZED ANNELATION REACTIONS .5. PALLADIUM-CATALYZED C-H ACTIVATION OF TERT-BUTYL GROUPS - A SIMPLE SYNTHESIS OF 1,2-DIHYDROCYCLOBUTABENZENE DERIVATIVES [J].
DYKER, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (01) :103-105
[9]   A general modular method of azaindole and thienopyrrole synthesis via Pd-catalyzed tandem couplings of gem-dichloroolefins [J].
Fang, Yuan-Qing ;
Yuen, Josephine ;
Lautens, Mark .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5152-5160
[10]  
Goldman A., 2004, American Chemical Society Symposium Series, V885, P1, DOI DOI 10.1021/BK-2004-0885.CH001