Iodine-catalysed regioselective thiolation of flavonoids using sulfonyl hydrazides as sulfenylation reagents

被引:36
|
作者
Zhao, Xia [1 ]
Deng, Zhijie [1 ]
Wei, Aoqi [1 ]
Li, Boyang [1 ]
Lu, Kui [2 ]
机构
[1] Tianjin Normal Univ, Tianjin Key Lab Struct & Performance Funct Mol, Key Lab Inorgan Organ Hybrid Funct Mat Chem, Coll Chem,Minist Educ, Tianjin 300387, Peoples R China
[2] Tianjin Univ Sci & Technol, Coll Biotechnol, Tianjin 300457, Peoples R China
基金
美国国家科学基金会;
关键词
FULLY SUBSTITUTED PYRAZOLES; ANTIOXIDANT ACTIVITY; ACTIVATED ALKENES; DERIVATIVES; INHIBITION; SULFONYLHYDRAZIDES; FUNCTIONALIZATION; ARYLSULFONYLATION; SULPHENYLATION; SURROGATE;
D O I
10.1039/c6ob01006g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iodine-catalysed regioselective sulfenylation of flavonoid derivatives with sulfonyl hydrazides was developed. Various flavonoid thioethers were obtained in moderate to good yield. The thiolation could be conveniently directed to C-8 for flavone, flavonol, dihydroflavone, and isoflavone derivatives or to C-7 for aurone derivatives by employing the isopropyl ethers of flavonoids bearing free OH groups at the C-5 or C-4 positions.
引用
收藏
页码:7304 / 7312
页数:9
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  • [1] Iodine-catalyzed thiolation of electron-rich aromatics using sulfonyl hydrazides as sulfenylation reagents
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    Li, Tianjiao
    Zhang, Lipeng
    Lu, Kui
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (03) : 1131 - 1137
  • [2] Iodine catalyzed regioselective sulfenylation of aminouracils with sulfonyl hydrazides
    Devi, Jutika
    Saikia, Nilakhy
    Choudhury, Gitashree
    Deka, Dibakar Chandra
    [J]. TETRAHEDRON LETTERS, 2021, 65
  • [3] Iodine-Catalyzed Regioselective Sulfenylation of Indoles with Sulfonyl Hydrazides
    Yang, Fu-Lai
    Tian, Shi-Kai
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (18) : 4929 - 4932
  • [4] Iodine-catalysed regioselective synthesis of β-hydroxysulfides
    Tehri, Piyush
    Aegurula, Balakrishna
    Peddinti, Rama Krishna
    [J]. TETRAHEDRON LETTERS, 2017, 58 (21) : 2062 - 2065
  • [5] Iodine-catalyzed regioselective thiolation of imidazo[1,2-a]pyridines using sulfonyl hydrazides as a thiol surrogate
    Bagdi, Avik Kumar
    Mitra, Shubhanjan
    Ghosh, Monoranjan
    Hajra, Alakananda
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (11) : 3314 - 3320
  • [6] Tetrabutylammonium Iodide-Promoted Thiolation of Oxindoles Using Sulfonyl Chlorides as Sulfenylation Reagents
    Zhao, Xia
    Wei, Aoqi
    Lu, Xiaoyu
    Lu, Kui
    [J]. MOLECULES, 2017, 22 (08)
  • [7] Catalyst-Free Regioselective Sulfenylation of Imidazoheterocycles with Sulfonyl Hydrazides in Water
    Chowdhury, Soumyadeep Roy
    Fadikar, Pulak
    Ul Hoque, Injamam
    Maity, Soumitra
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (02) : 332 - 336
  • [8] Potassium iodide promoted thiolation of pyrazolones and benzofurans using aryl sulfonyl chlorides as sulfenylation reagents
    Zhao, Xia
    Lu, Xiaoyu
    Wei, Aoqi
    Jia, Xiaoliang
    Chen, Jun
    Lu, Kui
    [J]. TETRAHEDRON LETTERS, 2016, 57 (48) : 5330 - 5333
  • [9] Iodine promoted sulfenylation of pyrrolo[1,2-a]quinoxalines a ]quinoxalines with sulfonyl hydrazides
    Ca, Thuy T.
    Dong, Y. N.
    Nguyen, Tung T.
    [J]. TETRAHEDRON LETTERS, 2024, 145
  • [10] Iodine-mediated sulfenylation of 4-hydroxycoumarins with sulfonyl hydrazides under aqueous conditions
    Yang, Zan
    Yan, Yueqiao
    Li, An
    Liao, Jiashu
    Zhang, Lei
    Yang, Tao
    Zhou, Congshan
    [J]. NEW JOURNAL OF CHEMISTRY, 2018, 42 (18) : 14738 - 14741