Selective Oxidation of Benzo[d]isothiazol-3(2H)-Ones Enabled by Selectfluor

被引:0
|
作者
Li, Qin [1 ]
Yuan, Dan [1 ]
Liu, Chong [2 ]
Herington, Faith [2 ]
Yang, Ke [1 ]
Ge, Haibo [2 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
[2] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
来源
MOLECULES | 2024年 / 29卷 / 16期
关键词
Selectfluor; oxidation; benzoisothiazol-3-one-1-oxide; DERIVATIVES;
D O I
10.3390/molecules29163899
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A metal-free and Selectfluor-mediated selective oxidation reaction of benzo[d]isothiazol-3(2H)-ones in aqueous media is presented. This novel strategy provides a facile, green, and efficient approach to access important benzo[d]isothiazol-3(2H)-one-1-oxides with excellent yields and high tolerance to various functional groups. Furthermore, the purification of benzoisothiazol-3-one-1-oxides does not rely on column chromatography. Moreover, the preparation of saccharine derivatives has been achieved through sequential, double oxidation reactions in a one-pot aqueous media.
引用
收藏
页数:15
相关论文
共 50 条
  • [11] RING TRANSFORMATION OF 2-SUBSTITUTED ISOTHIAZOL-3(2H)-ONES TO 3,4-DIHYDRO-1,3-THIAZIN-4(2H)-ONES BY A NOVEL CARBENE ADDITION RING EXPANSION SEQUENCE
    CROW, WD
    GOSNEY, I
    ORMISTON, RA
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (11) : 643 - 644
  • [12] 2-(4-Nitrophenyl)isothiazol-3(2H)-one: A Promising Selective Agent against Hepatocellular Carcinoma Cells
    Marka, Sofia
    Zografaki, Maria-Eleftheria
    Tsolomiti, Georgia
    Kalliampakou, Katerina I.
    Tsolomitis, Athanasios
    Koumantou, Christina
    Smirlis, Despina
    Vassilaki, Niki
    Kintzios, Spyros
    PHARMACEUTICALS, 2024, 17 (06)
  • [13] 2-(3-Hydroxybenzyl)benzo[d]isothiazol-3(2H)-one Mannich base derivatives as potential multifunctional anti-Alzheimer’s agents
    Yuxi He
    Ganyuan Xiao
    Guangjun Yu
    Qing Song
    Heng Zhang
    Zhuoling Liu
    Zhenghuai Tan
    Yong Deng
    Medicinal Chemistry Research, 2021, 30 : 1249 - 1264
  • [14] 2-(3-Hydroxybenzyl)benzo[d]isothiazol-3(2H)-one Mannich base derivatives as potential multifunctional anti-Alzheimer's agents
    He, Yuxi
    Xiao, Ganyuan
    Yu, Guangjun
    Song, Qing
    Zhang, Heng
    Liu, Zhuoling
    Tan, Zhenghuai
    Deng, Yong
    MEDICINAL CHEMISTRY RESEARCH, 2021, 30 (06) : 1249 - 1264
  • [15] N-[(3-methyl-1-phenylsulfonyl-1H-indol-2-yl)methyl]-1,1-dioxo-1-benzo[d] isothiazol-3(2H)-one
    Palani, K.
    Ponnuswamy, M. N.
    Jaisankar, P.
    Srinivasan, P. C.
    Nethaji, M.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O2026 - O2028
  • [16] Copper-catalysed one-pot synthesis of N-substituted benzo[d]isothiazol-3(2H)-ones via C-S/N-S bond formation
    Paul, Rajesh
    Punniyamurthy, Tharmalingam
    RSC ADVANCES, 2012, 2 (18) : 7057 - 7060
  • [17] Synthesis and Bioactivity of 2-((5-Mercapto-1, 3, 4-Oxadiazol-2-yl) Methyl) Benzo[d] Isothiazol-3(2H)-One as Potential Microbiocide
    Xu, Fengling
    Lin, Cunguo
    Lin, Qiang
    NEW AND ADVANCED MATERIALS, PTS 1 AND 2, 2011, 197-198 : 174 - +
  • [18] TILCOTIL STUDIES [3+2] ADDITIONS WITH ISOTHIAZOL-3(2H)-ONE 1,1-DIOXIDE
    BURRI, KF
    HELVETICA CHIMICA ACTA, 1989, 72 (06) : 1416 - 1427
  • [19] PHOTOISOMERIZATION OF "2-SUBSTITUTED-ISOTHIAZOL-3(2H)-ONES TO 3-SUBSTITUTED-THIAZOL-2(3H)-ONES
    ROKACH, J
    HAMEL, P
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (18) : 786 - 787
  • [20] TILCOTIL STUDIES .2. [4 + 2] ADDITIONS WITH ISOTHIAZOL-3(2H)-ONE 1,1-DIOXIDE
    BURRI, KF
    HELVETICA CHIMICA ACTA, 1990, 73 (01) : 69 - 80