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Direct nucleophilic difluoromethylation of aromatic isoxazoles activated by electron-withdrawing groups using (difluoromethyl)trimethylsilane

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      Abstract

      The activation of aromatic diaryl isoxazoles with strong electron-withdrawing groups, such as the nitro, triflyl, and the phenylsulfonyl groups, at the 4-position has enabled the first regio- and diastereoselective difluoromethylation at the 5-position of isoxazoles by nucleophilic addition using (difluoromethyl) trimethylsilane, Me3SiCF2H, to provide difluoromethylated isoxazolines in good yields. Conjugated styryl-4-nitroisoxazoles were also nicely converted into the corresponding CF2H adducts with high regio- and excellent diastereoselectivities. Since the trifluoromethylated analogs of the corresponding diaryl-isoxazolines are effective ectoparasiticides, represented by fluralaner, should a series of difluoromethylated isoxazolines be obtained, they would be of great importance as promising drug candidates in this field.

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          Tetrahedron report number 221

           John Welch (1987)
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            Author and article information

            Affiliations
            [1 ]Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, Japan
            [2 ]Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, Japan
            Author notes
            [* ]Corresponding author's e-mail address: nozshiba@ 123456nitech.ac.jp

            Dedication: To Professor Iwao Ojima for his 70th birthday.

            Contributors
            (View ORCID Profile)
            Journal
            SOR-CHEM
            ScienceOpen Research
            ScienceOpen
            2199-1006
            18 December 2014
            : 0 (ID: aeab23b4-61ff-4936-a252-0cd98d9fddcf )
            : 0
            : 1-7
            2276:XE
            10.14293/S2199-1006.1.SOR-CHEM.AD1QVW.v1
            © 2014 Xin Wang et al.

            This work has been published open access under Creative Commons Attribution License CC BY 4.0 , which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Conditions, terms of use and publishing policy can be found at www.scienceopen.com .

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            Figures: 6, Tables: 3, References: 67, Pages: 7
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