Synthesis of Nitro-Functionalized Isoquinolinediones via NaNO2/Na2S2O8-Mediated Arylnitration of Alkenes

被引：3
|
作者：
Zhang, Lingling [1 ]
Wang, Zhi [2 ]
Wu, Jian [1 ]
Li, Xiaoqing [2 ]
机构：
[1] Jiangsu Acad Environm Ind & Technol Corp, Nanjing 210019, Peoples R China
[2] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 41卷 / 04期
关键词：
alkenes; arylnitration; cyclization; nitro radical; isoquinolinediones; METAL-FREE; CATALYZED ARYLSULFONYLATION; ACTIVATED ALKENES; NITRATION;
D O I：
10.6023/cjoc202010014
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new method for the synthesis of nitro-functionalized isoquinolinediones by arylnitration of methacryloylbenzamides has been reported. Readily accessible NaNO2/Na2S2O8 was used as nitro radical precursor, and 18-crown-6 was used to promote the reaction. Compared with the existing method, this method is not only environmentally friendly but also easy to operate.
引用
收藏
页码：1734 / 1738
页数：5
相关论文
共 22 条
  • [1] CONJUGATED NITROALKENES - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS
    BARRETT, AGM
    GRABOSKI, GG
    [J]. CHEMICAL REVIEWS, 1986, 86 (05) : 751 - 762
  • [2] Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry
    Basavaiah, Deevi
    Reddy, Bhavanam Sekhara
    Badsara, Satpal Singh
    [J]. CHEMICAL REVIEWS, 2010, 110 (09) : 5447 - 5674
  • [3] Magnesium Chelating 2-Hydroxyisoquinoline-1,3(2H,4H)-diones, as Inhibitors of HIV-1 Integrase and/or the HIV-1 Reverse Transcriptase Ribonuclease H Domain: Discovery of a Novel Selective Inhibitor of the Ribonuclease H Function
    Billamboz, Muriel
    Bailly, Fabrice
    Lion, Cedric
    Touati, Nadia
    Vezin, Herve
    Calmels, Christina
    Andreola, Marie-Line
    Christ, Frauke
    Debyser, Zeger
    Cotelle, Philippe
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (06) : 1812 - 1824
  • [4] A novel transition metal free [bis-(trifluoroacetoxy)iodo]benzene (PIFA) mediated oxidative ipso nitration of organoboronic acids
    Chatterjee, Nachiketa
    Bhatt, Divya
    Goswami, Avijit
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (17) : 4828 - 4832
  • [5] Recent Advances in Transition-Metal-Catalyzed Directing Group Assisted Nitration of Inert C-H Bonds
    Cheng, Huicheng
    Lin, Jinlong
    Zhang, Yaofeng
    Chen, Bing
    Wang, Min
    Cheng, Lihua
    Ma, Jiaoli
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (02) : 318 - 327
  • [6] Visible-Light-Mediated Nitration of Protected Anilines
    Duesel, Simon J. S.
    Koenig, Burkhard
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (05) : 2802 - 2807
  • [7] Monomeric Octahedral Ruthenium(II) Complex Enabled meta-C-H Nitration of Arenes with Removable Auxiliaries
    Fan, Zhoulong
    Li, Jie
    Lu, Heng
    Wang, Dong-Yu
    Wang, Chao
    Uchiyama, Masanobu
    Zhang, Ao
    [J]. ORGANIC LETTERS, 2017, 19 (12) : 3199 - 3202
  • [8] Regio- and Chemoselective Mono- and Bisnitration of 8-Amino quinoline Amides with Fe(NO3)3•9H2O as Promoter and Nitro Source
    He, Yan
    Zhao, Ningning
    Qiu, Liqi
    Zhang, Xinying
    Fan, Xuesen
    [J]. ORGANIC LETTERS, 2016, 18 (23) : 6054 - 6057
  • [9] Recent advances in nitro-involved radical reactions
    Huang, Jiapian
    Ding, Feng
    Rojsitthisak, Pornchai
    He, Fu-Sheng
    Wu, Jie
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (18) : 2873 - 2898
  • [10] Li XQ, 2006, CHINESE J ORG CHEM, V26, P1111
123