Direct C3 Carbamoylation of 2H-Indazoles

被引：18

作者：

Bhat, Vighneshwar Shridhar ^{[1
]}

Lee, Anna ^{[1
]}

机构：

[1] Jeonbuk Natl Univ, Dept Chem, Jeonju 54896, South Korea

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 23期

基金：

新加坡国家研究基金会;

关键词：

Carbamoylation; 2H-Indazoles; Minisci reaction; Radical reaction; Synthetic methods; PHOTOREDOX CATALYSIS; INDAZOLES; FUNCTIONALIZATION; DERIVATIVES; INHIBITORS; RADICALS; DESIGN; LIGHT;

D O I：

10.1002/ejoc.202100461

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed a novel method for direct C3 carbamoylation of 2H-indazoles using oxamic acids as carbamoyl radical sources. In the presence of ammonium persulfate, carbamoyl radicals were generated from oxamic acids, then used for further reactions with 2H-indazoles to afford the desired products. The reaction proceeds under metal- and catalyst-free conditions. This simple process allows for the efficient synthesis of C3 carbamoylated 2H-indazoles, which are important scaffolds in organic synthesis.

引用

页码：3382 / 3385

页数：4

共 51 条

[1] Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis [J].

Afewerki, Samson ;

Cordova, Armando .

CHEMICAL REVIEWS, 2016, 116 (22) :13512-13570

[2] Visible-light-mediated direct C3-arylation of 2H-indazoles enabled by an electron-donor-acceptor complex [J].

Aganda, Kim Christopher C. ;

Kim, Junyoung ;

Lee, Anna .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (45) :9698-9702

[3] 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

[4] Carbamoyl Radicals via Photoredox Decarboxylation of Oxamic Acids in Aqueous Media: Access to 3,4-Dihydroquinolin-2(1H)-ones [J].

Bai, Qa-Fan ;

Jin, Chengan ;

He, Jing-Yao ;

Feng, Gaofeng .

ORGANIC LETTERS, 2018, 20 (08) :2172-2175

[5] Carbamoyl Radical-Mediated Synthesis and Semipinacol Rearrangement of b-Lactam Diols [J].

Betou, Marie ;

Male, Louise ;

Steed, Jonathan W. ;

Grainger, Richard S. .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (21) :6505-6517

[6] Direct C3 Carbamoylation of 2H-Indazoles [J].

Bhat, Vighneshwar Shridhar ;

Lee, Anna .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (23) :3382-3385

[7] Direct Acyl Radical Addition to 2H-Indazoles Using Ag-Catalyzed Decarboxylative Cross-Coupling of α-Keto Acids [J].

Bogonda, Ganganna ;

Kim, Hun Young ;

Oh, Kyungsoo .

ORGANIC LETTERS, 2018, 20 (09) :2711-2715

[8] Optimization of a pyrazoloquinolinone class of Chk1 kinase inhibitors [J].

Brnardic, Edward J. ;

Garbaccio, Robert M. ;

Fraley, Mark E. ;

Tasber, Edward S. ;

Steen, Justin T. ;

Arrington, Kenneth L. ;

Dudkin, Vadim Y. ;

Hartman, George D. ;

Stirdivant, Steven M. ;

Drakas, Bob A. ;

Rickert, Keith ;

Walsh, Eileen S. ;

Hamilton, Kelly ;

Buser, Carolyn A. ;

Hardwick, James ;

Tao, Weikang ;

Beek, Stephen C. ;

Mao, Xianzhi ;

Lobell, Robert B. ;

Sepp-Lorenzino, Laura ;

Yan, Youwei ;

Ikuta, Mari ;

Munshi, Sanjeev K. ;

Kuo, Lawrence C. ;

Kreatsoulas, Constantine .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (21) :5989-5994

[9] Copper-Catalyzed Direct Carbamoylation of Quinoxalin-2(1H)-ones with Hydrazinecarboxamides Under Mild Conditions [J].

Chu, Xianglong ;

Wu, Yujuan ;

Lu, Haigen ;

Yang, Bingchuan ;

Ma, Chen .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (09) :1141-1144

[10] Indazole estrogens:: Highly selective ligands for the estrogen receptor β [J].

De Angelis, M ;

Stossi, F ;

Carlson, KA ;

Katzenellenbogen, BS ;

Katzenellenbogen, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (04) :1132-1144

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