Imino-λ3-iodane-Triggered Oxidative Ring-Opening of 2H-Indazoles to ortho-N-Acylsulfonamidated Azobenzenes

被引：8

作者：

Bhattacharjee, Suvam ^{[1
]}

Hajra, Alakananda ^{[1
]}

机构：

[1] Dept Chem, 30190 Visva Bharati, Santini Ketan 731235, West Bengal, India

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 22期

关键词：

METAL-FREE; AMINATION; CHEMISTRY; ANALOGS; OXIDES;

D O I：

10.1021/acs.orglett.3c01498

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iminoiodane-enabled oxidative ring-opening of 2H-indazoles via C-N bond cleavage has been developedundermetal-free reaction conditions. This methodology afforded a new arrayof unsymmetrical ortho-N-acylsulfonamidatedazobenzenes with a wide functional group tolerance in good yields.The reaction potentially proceeds through the formation of a zwitterionicadduct, which is formed by the reaction between 2H-indazoles and iminoiodane.

引用

页码：4183 / 4187

页数：5

共 53 条

[11] Electrochemically Enabled Dehydrogenative Phosphorothiolation of 2H-Indazoles under Electrolyte-Free Conditions
Ghosh, Payel
Hajra, Alakananda
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (23) : 4157 - 4165
[12] A combined experimental and theoretical study on the reactivity of nitrenes and nitrene radical anions
Guo, Yujing
Pei, Chao
Koenigs, Rene M.
[J]. NATURE COMMUNICATIONS, 2022, 13 (01)
[13] Synthesis of N-Sulfonylamidated and Amidated Azobenzenes under Rhodium Catalysis
Han, Sangil
Mishra, Neeraj Kumar
Sharma, Satyasheel
Park, Jihye
Choi, Miji
Lee, Seok-Yong
Oh, Joa Sub
Jung, Young Hoon
Kim, In Su
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (16) : 8026 - 8035
[14] Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds with Hypervalent Iodine Reagents
Hari, Durga Prasad
Waser, Jerome
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (07) : 2190 - 2193
[15] Azobenzene-containing, peptidyl α-ketoesters as photobiological switches of α-chymotrypsin
Harvey, AJ
Abell, AD
[J]. TETRAHEDRON, 2000, 56 (50) : 9763 - 9771
[16] Cobalt(III)-Catalyzed Synthesis of Indazoles and Furans by C-H Bond Functionalization/Addition/Cyclization Cascades
Hummel, Joshua R.
Ellman, Jonathan A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) : 490 - 498
[17] Hunger K., 2002, IND DYES CHEM PROPER
[18] Design, Synthesis and Biological Evaluation of Pazopanib Derivatives as Antitumor Agents
Jia, Yuping
Zhang, Jian
Feng, Jinhong
Xu, Fuming
Pan, Huili
Xu, Wenfang
[J]. CHEMICAL BIOLOGY & DRUG DESIGN, 2014, 83 (03) : 306 - 316
[19] Visible Light-Enhanced C-H Amination of Cyclic Ethers with Iminoiodinanes
Jurberg, Igor D.
Nome, Rene A.
Crespi, Stefano
Atvars, Teresa D. Z.
Koenig, Burkhard
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (23) : 4061 - 4068
[20] Zwitterionic carbene adducts and their carbene isomers
Kelemen, Z.
Streubel, R.
Nyulaszi, L.
[J]. RSC ADVANCES, 2015, 5 (52) : 41795 - 41802

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