Ru(II)-catalyzed α-sulfonamidation of cyclic β-ketoesters with sulfonyl azides

被引:1
|
作者
Rao, M. V. Krishna [1 ,3 ]
Reddy, K. Nagarjuna [1 ,3 ]
Sridhar, B. [2 ]
Reddy, B. V. Subba [1 ]
机构
[1] CSIR Indian Inst Chem Technol, Ctr Semiochem, Hyderabad 500007, Telangana, India
[2] CSIR Indian Inst Chem Technol, Lab Xray Crystallog, Hyderabad 500007, Telangana, India
[3] Acad Sci & Innovat Res AcSIR, New Delhi 110025, India
关键词
Transition metal catalysis; Cyclic beta-ketoesters; Sulfonyl azides; alpha-Sulfonamidation; KETO-ESTERS; 1,3-DICARBONYL COMPOUNDS; TRANSFER HYDROGENATION; LEAD-TETRAACETATE; DIRECT AMINATION; RING-EXPANSION; LIGANDS; DICHLOROMETHANE; HYDROXYLATION; DERIVATIVES;
D O I
10.1016/j.tetlet.2019.151083
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha-Sulfonamidation of beta-ketoesters with sulfonyl azide has been developed for the first time using a catalytic amount of Ru(II) complex to produce the 1-oxo-2-(sulfonamido)-2,3-dihydro-1H-indene-2-carboxylate and 1-oxo-2-(sulfonamido)-1,2,3,4-tetrahydronaphthalene-2-carboxylate derivatives in good yields. This method also works well with alpha-iodotetralones to afford the N-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulphonamide derivatives under similar conditions. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 50 条
  • [1] Iridium(III)-Catalyzed Benzylic Amine Directed C-H Sulfonamidation of Arenes with Sulfonyl Azides
    Chen, Heng
    Huestis, Malcolm P.
    CHEMCATCHEM, 2015, 7 (05) : 743 - 746
  • [2] Ru(II)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides
    Bhanuchandra, M.
    Yadav, M. Ramu
    Rit, Raja K.
    Kuram, Malleswara Rao
    Sahoo, Akhila K.
    CHEMICAL COMMUNICATIONS, 2013, 49 (45) : 5225 - 5227
  • [3] Ru(II)-Catalyzed Selective C-H Amination of Xanthones and Chromones with Sulfonyl Azides: Synthesis and Anticancer Evaluation
    Shin, Youngmi
    Han, Sangil
    De, Umasankar
    Park, Jihye
    Sharma, Satyasheel
    Mishra, Neeraj Kumar
    Lee, Eui-Kyung
    Lee, Youngil
    Kim, Hyung Sik
    Kim, In Su
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19): : 9262 - 9271
  • [4] Cobalt(II)-Catalyzed Isocyanide Insertion Reaction with Sulfonyl Azides in Alcohols: Synthesis of Sulfonyl Isoureas
    Jiang, Tian
    Gu, Zheng-Yang
    Yin, Ling
    Wang, Shun-Yi
    Ji, Shun-Jun
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (15): : 7913 - 7919
  • [5] Iridium-catalyzed regioselective C-H sulfonamidation of 1,2,4-thiadiazoles with sulfonyl azides in water
    Cao, Xian-Ting
    Wei, Su-Ning
    Sun, Hao-Tian
    Li, Meng
    Zheng, Zuo-Ling
    Wang, Guannan
    RSC ADVANCES, 2021, 11 (36) : 22000 - 22004
  • [6] RuII-Catalyzed ortho-Sulfonamidation of -Tetralones with Sulfonyl Azides and Synthesis of Sivelestat by Aromatic C-H Activation
    Rao, Medikonda V. Krishna
    Reddy, Keesari Nagarjuna
    Sridhar, Balasubramaniam
    Reddy, Basi V. Subba
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (12) : 1851 - 1856
  • [7] Iridium-Catalyzed Direct Ortho-C-H Amidation of ?-Ketoesters with Sulfonyl Azides Using a Transient Directing Group Strategy
    He, Yinlong
    Sun, Bing
    Lu, Xuelian
    Zhou, Yirong
    Zhang, Fang -Lin
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (07): : 4345 - 4351
  • [8] Synthesis of Cyclic Amidines by Iridium-Catalyzed Deoxygenative Reduction of Lactams and Tandem Reaction with Sulfonyl Azides
    He, Youliang
    Wang, Xiaoming
    ORGANIC LETTERS, 2021, 23 (01) : 225 - 230
  • [9] Iridium(III)-Catalyzed Direct C-H Sulfonamidation of 2-Aryl-1,2,3-triazole N-Oxides with Sulfonyl Azides
    Zhu, Bingfeng
    Cui, Xiuling
    Pi, Chao
    Chen, Dong
    Wu, Yangjie
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (02) : 326 - 332
  • [10] Ru-catalyzed direct C-H amidation of 2-arylbenzo[d]thiazoles with sulfonyl azides
    Zhou, Xiaoli
    Luo, Puying
    Long, Ling
    Ouyang, Meizhen
    Sang, Xiaoyan
    Ding, Qiuping
    TETRAHEDRON, 2014, 70 (38) : 6742 - 6748