Iron promoted C3-H nitration of 2H-indazole: direct access to 3-nitro-2H-indazoles

被引:44
|
作者
Murugan, Arumugavel [1 ]
Gorantla, Koteswar Rao [1 ]
Mallik, Bhabani S. [1 ]
Sharada, Duddu S. [1 ]
机构
[1] Indian Inst Technol Hyderabad, Dept Chem, Sangareddy 502285, Telangana, India
关键词
C-H FUNCTIONALIZATION; CATALYZED REMOTE C; BOND ACTIVATION; THERMAL-DECOMPOSITION; NITROGEN-HETEROCYCLES; RADICAL NITRATION; ORGANIC-SYNTHESIS; ALKALOID ANALOGS; HYBRID MOLECULES; DERIVATIVES;
D O I
10.1039/c8ob00931g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient C3-H functionalization of indazole has been demonstrated. Notably, this method involves chelation-free radical C-H nitration on 2H-indazole. The radical mechanism was confirmed by control experiments and quantum chemical calculations. The synthetic utility has been proven by the synthesis of bio-relevant benzimidazoindazoles via reductive cyclization.
引用
收藏
页码:5113 / 5118
页数:6
相关论文
共 50 条
  • [1] Visible-Light-Promoted Direct C3-H Cyanomethylation of 2H-Indazoles
    Mi, Xia
    Cui, Beibei
    Song, Jinqing
    Zhang, Jingyu
    ACS OMEGA, 2023, 8 (12): : 11192 - 11200
  • [2] Regioselective C3-H Trifluoromethylation of 2H-Indazole under Transition-Metal-Free Photoredox Catalysis
    Murugan, Arumugavel
    Babu, Venkata Nagarjuna
    Polu, Ashok
    Sabarinathan, Nagaraj
    Bakthadoss, Manickam
    Sharada, Duddu S.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12): : 7796 - 7803
  • [3] Electrochemically Promoted Regioselective C3-H Trifluoro/Difluoromethylation of 2H -Indazoles at Room Temperature
    Behera, Mousumi
    Sahu, Ajit Kumar
    Shukla, Shubham Y.
    Bhat, Ramakrishna G.
    SYNLETT, 2024, 35 (20) : 2547 - 2553
  • [4] PHOTOCHEMISTRY OF 1H-INDAZOLE AND 2H-INDAZOLE IN ACIDIC SOLUTION
    GEORGARAKIS, E
    SCHMID, H
    HANSEN, HJ
    HELVETICA CHIMICA ACTA, 1979, 62 (01) : 234 - 270
  • [5] Electrochemical regioselective C-H selenylation of 2H-indazole derivatives
    Lin, Shengsheng
    Cheng, Xiaomei
    Hasimujiang, Balati
    Xu, Zhongnan
    Li, Fengtan
    Ruan, Zhixiong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 20 (01) : 117 - 121
  • [6] 1H-Indazole and 2H-indazole derivatives of androsta-5,16-dien-3β-ol
    Silva, Manuela Ramos
    Moreira, Vania M.
    Cardoso, Claudia
    Beja, Ana Matos
    Salvador, Jorge A. R.
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2008, 64 : O217 - O219
  • [7] Electrochemically promoted C-3 amination of 2H-indazoles
    Sun, Mingli
    Zhou, Yuhui
    Li, Laiqiang
    Wang, Lei
    Ma, Yongmin
    Li, Pinhua
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (04): : 754 - 759
  • [8] Iron-Catalyzed Direct C3-H Trifluoromethylthiolation of Quinoxalin-2(1H)-ones
    Chen, Xiaoyu
    Geng, Yang
    Zhu, Yu
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (02) : 214 - 219
  • [9] Direct C3 Carbamoylation of 2H-Indazoles
    Bhat, Vighneshwar Shridhar
    Lee, Anna
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (23) : 3382 - 3385
  • [10] INDAZOLE STUDIES .3. THE BROMINATION OF 2-PHENYL-2H-INDAZOLE - FORMATION AND STRUCTURE DETERMINATION OF MONOBROMO-2-PHENYL-2H-INDAZOLES, DIBROMO-2-PHENYL-2H-INDAZOLES, AND TRIBROMO-2-PHENYL-2H-INDAZOLES
    WAALWIJK, PS
    COHENFERNANDES, P
    HABRAKEN, CL
    JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (18): : 3401 - 3403