Direct C3 Carbamoylation of 2H-Indazoles

被引：16

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

[31] Direct Arylations of 2H-Indazoles On Water
Ohnmacht, Stephan A.
Culshaw, Andrew J.
Greaney, Michael F.
[J]. ORGANIC LETTERS, 2010, 12 (02) : 224 - 226
[32] Synthesis and Biological Evaluation of 2H-Indazole Derivatives: Towards Antimicrobial and Anti-Inflammatory Dual Agents
Perez-Villanueva, Jaime
Yepez-Mulia, Lilian
Gonzalez-Sanchez, Ignacio
Palacios-Espinosa, Juan Francisco
Soria-Arteche, Olivia
Sainz-Espunes, Teresita del Rosario
Cerbon, Marco A.
Rodriguez-Villar, Karen
Rodriguez-Vicente, Ana Karina
Cortes-Gines, Miguel
Custodio-Galvan, Zeltzin
Estrada-Castro, Dante B.
[J]. MOLECULES, 2017, 22 (11):
[33] Photoredox-Catalyzed Reductive Carbamoyl Radical Generation: A Redox-Neutral Intermolecular Addition-Cyclization Approach to Functionalized 3,4-Dihydroquinolin-2-ones
Petersen, Wade F.
Taylor, Richard J. K.
Donald, James R.
[J]. ORGANIC LETTERS, 2017, 19 (04) : 874 - 877
[34] Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis
Prier, Christopher K.
Rankic, Danica A.
MacMillan, David W. C.
[J]. CHEMICAL REVIEWS, 2013, 113 (07) : 5322 - 5363
[35] Proctor R.S.J., 2019, ANGEW CHEM, V131, P13802, DOI DOI 10.1002/ANGE.201900977
[36] Recent Advances in Minisci-Type Reactions
Proctor, Rupert S. J.
Phipps, Robert J.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (39) : 13666 - 13699
[37] Organic Photoredox Catalysis
Romero, Nathan A.
Nicewicz, David A.
[J]. CHEMICAL REVIEWS, 2016, 116 (17) : 10075 - 10166
[38] Recent advances in the chemistry of indazoles
Schmidt, Andreas
Beutler, Ariane
Snovvdovych, Bohdan
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (24) : 4073 - 4095
[39] Solar Synthesis: Prospects in Visible Light Photocatalysis
Schultz, Danielle M.
Yoon, Tehshik P.
[J]. SCIENCE, 2014, 343 (6174) : 985 - +
[40] Photoredox functionalization of C-H bonds adjacent to a nitrogen atom
Shi, Lei
Xia, Wujiong
[J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (23) : 7687 - 7697

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