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

被引：9

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

[1] Photochromic Blockers of Voltage-Gated Potassium Channels [J].

Banghart, Matthew R. ;

Mourot, Alexandre ;

Fortin, Doris L. ;

Yao, Jennifer Z. ;

Kramer, Richard H. ;

Trauner, Dirk .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9097-9101

[2] Hypervalent iodine(iii)-mediated oxidative dearomatization of 2H-indazoles towards indazolyl indazolones [J].

Bhattacharjee, Suvam ;

Laru, Sudip ;

Hajra, Alakananda .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (45) :8893-8897

[3] Remote difunctionalization of 2H-indazoles using Koser's reagents [J].

Bhattacharjee, Suvam ;

Laru, Sudip ;

Hajra, Alakananda .

CHEMICAL COMMUNICATIONS, 2022, 58 (07) :981-984

[4] A Roadmap to Success in Photopharmacology [J].

Broichhagen, Johannes ;

Frank, James Allen ;

Trauner, Dirk .

ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (07) :1947-1960

[5] Transition metal-free and regioselective vinylation of phosphine oxides and H-phosphinates with VBX reagents [J].

Castoldi, Laura ;

Rajkiewicz, Adam A. ;

Olofsson, Berit .

CHEMICAL COMMUNICATIONS, 2020, 56 (92) :14389-14392

[6] Organocatalytic nitrenoid transfer: metal-free selective intermolecular C(sp3)-H amination catalyzed by an iminium salt [J].

Combee, Logan A. ;

Raya, Balaram ;

Wang, Daoyong ;

Hilinski, Michael K. .

CHEMICAL SCIENCE, 2018, 9 (04) :935-939

[7] New color chemosensors for monosaccharides based on Azo dyes [J].

DiCesare, N ;

Lakowicz, JR .

ORGANIC LETTERS, 2001, 3 (24) :3891-3893

[8]

Dohi T, 2015, IODINE CHEMISTRY AND APPLICATIONS, P103

[9]

García-Vázquez V, 2022, chemRxiv, DOI [10.26434/chemrxiv-2022-vbc0x, 10.26434/chemrxiv-2022-vbc0x, DOI 10.26434/CHEMRXIV-2022-VBC0X]

[10] Rhenium-catalyzed C-H aminocarbonylation of azobenzenes with isocyanates [J].

Geng, Xiaoyu ;

Wang, Congyang .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (28) :7619-7623

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