Direct Acyl Radical Addition to 2H-Indazoles Using Ag-Catalyzed Decarboxylative Cross-Coupling of α-Keto Acids

被引:105
作者
Bogonda, Ganganna [1 ]
Kim, Hun Young [1 ]
Oh, Kyungsoo [1 ]
机构
[1] Chung Ang Univ, Ctr Metareceptome Res, Coll Pharm, 84 Heukseok Ro, Seoul 06974, South Korea
基金
新加坡国家研究基金会;
关键词
N BOND FORMATION; INDAZOLE DERIVATIVES; OXOCARBOXYLIC ACIDS; SUBSTITUTED; 3-AMINOINDAZOLES; PHOTOREDOX CATALYSIS; EFFICIENT SYNTHESIS; CARBOXYLIC-ACIDS; ACYLATION; DESIGN; ARYNES;
D O I
10.1021/acs.orglett.8b00920
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A direct acyl radical addition to 2H-indazoles has been achieved for the first time, where the less-aromatic quinonoid 2H-indazoles readily accepted radical species to the C-3 position. Motivated by the lack of direct acylation strategy for 2H-indazoles, the current method utilizes the radical acceptability of 2H-indazoles, discovering an ambient temperature reaction to provide facile access to a diverse array of 3-aryl-2H-indazoles with three points of structural diversification in 25%-83% yields.
引用
收藏
页码:2711 / 2715
页数:5
相关论文
共 64 条
[1]   PALLADIUM COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION OF NITROARENES - NOVEL SYNTHESIS OF INDOLE AND 2H-INDAZOLE DERIVATIVES [J].
AKAZOME, M ;
KONDO, T ;
WATANABE, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3375-3380
[2]   Discovery of highly selective CRAF inhibitors, 3-carboxamido-2H-indazole-6-arylamide: In silico FBLD design, synthesis and evaluation [J].
Aman, Waqar ;
Lee, Junghun ;
Kim, Minjung ;
Yang, Songyi ;
Jung, Hoyong ;
Hah, Jung-Mi .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (04) :1188-1192
[3]   Solution to the C3-Arylation of Indazoles: Development of a Scalable Method [J].
Basu, Kallol ;
Poirier, Marc ;
Ruck, Rebecca T. .
ORGANIC LETTERS, 2016, 18 (13) :3218-3221
[4]   Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible-Light Photoredox Catalysis [J].
Bergonzini, Giulia ;
Cassani, Carlo ;
Wallentin, Carl-Johan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) :14066-14069
[5]   Design, Synthesis, and Use of Y-Shaped ATRP/NMP Surface Tethered Initiator [J].
Calabrese, David R. ;
Ditter, David ;
Liedel, Clemens ;
Blumfield, Amit ;
Zentel, Rudolf ;
Ober, Christopher K. .
ACS MACRO LETTERS, 2015, 4 (06) :606-610
[6]   ACIDITY AND BASICITY OF INDAZOLE AND ITS N-METHYL DERIVATIVES IN THE GROUND AND IN THE EXCITED-STATE [J].
CATALAN, J ;
DELVALLE, JC ;
CLARAMUNT, RM ;
BOYER, G ;
LAYNEZ, J ;
GOMEZ, J ;
JIMENEZ, P ;
TOMAS, F ;
ELGUERO, J .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (41) :10606-10612
[7]   Importance of aromaticity on the relative stabilities of indazole annular tautomers: An ab initio study [J].
Catalan, J ;
dePaz, JLG ;
Elguero, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (01) :57-60
[8]   Pharmacological properties of indazole derivatives:: Recent developments [J].
Cerecetto, H ;
Gerpe, A ;
González, M ;
Arán, VJ ;
de Ocáriz, CO .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2005, 5 (10) :869-878
[9]   Chemistry of acyl radicals [J].
Chatgilialoglu, C ;
Crich, D ;
Komatsu, M ;
Ryu, I .
CHEMICAL REVIEWS, 1999, 99 (08) :1991-2069
[10]   Switchable Synthesis of 3-Substituted 1H-Indazoles and 3,3-Disubstituted 3H-Indazole-3-phosphonates Tuned by Phosphoryl Groups [J].
Chen, Guihua ;
Hu, Minglin ;
Peng, Yungui .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (03) :1591-1597