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
收藏
页码：4183 / 4187
页数：5
相关论文
共 53 条
  • [31] Metal-Free Intramolecular Aziridination of Alkenes Using Hypervalent Iodine Based Sulfonyliminoiodanes
    Moriarty, Robert M.
    Tyagi, Sachin
    [J]. ORGANIC LETTERS, 2010, 12 (02) : 364 - 366
  • [32] Oxidative Heterocycle Formation Using Hypervalent Iodine(III) Reagents
    Murarka, Sandip
    Antonchick, Andrey P.
    [J]. HYPERVALENT IODINE CHEMISTRY, 2016, 373 : 75 - 104
  • [33] N-Tosylcarboxamide as a Transformable Directing Group for Pd-Catalyzed C-H Ortho-Arylation
    Peron, Florent
    Fossey, Christine
    Cailly, Thomas
    Fabis, Frederic
    [J]. ORGANIC LETTERS, 2012, 14 (07) : 1827 - 1829
  • [34] Synthesis of nucleoside analogues in a ball mill: fast, chemoselective and high yielding acylation without undesirable solvents
    Ravalico, Francesco
    James, Stuart L.
    Vyle, Joseph S.
    [J]. GREEN CHEMISTRY, 2011, 13 (07) : 1778 - 1783
  • [35] Intermolecular Allene Functionalization by Silver-Nitrene Catalysis
    Rodriguez, Manuel R.
    Besora, Maria
    Molina, Francisco
    Maseras, Feliu
    Mar Diaz-Requejo, M.
    Perez, Pedro J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (30) : 13062 - 13071
  • [36] RUNTI C, 1985, INT J TISSUE REACT, V7, P175
  • [37] Metal-Free [2+2+1] Annulation of Alkynes, Nitriles and Nitrogen Atoms from Iminoiodanes for Synthesis of Highly Substituted Imidazoles
    Saito, Akio
    Kambara, Yui
    Yagyu, Takuma
    Noguchi, Keiichi
    Yoshimura, Akira
    Zhdankin, Viktor V.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (04) : 667 - 671
  • [38] CARBONYL OXIDES - ZWITTERIONS OR DIRADICALS
    SANDER, W
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (04): : 344 - 354
  • [39] Recent advances in the chemistry of indazoles
    Schmidt, Andreas
    Beutler, Ariane
    Snovvdovych, Bohdan
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (24) : 4073 - 4095
  • [40] Metal-free C-H Activation over Graphene Oxide toward Direct Syntheses of Structurally Different Amines and Amides in Water
    Shukla, Prashant
    Asati, Ambika
    Bhardiya, Smita R.
    Singh, Manorama
    Rai, Vijai K.
    Rai, Ankita
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (23) : 15552 - 15561
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