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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, Me 3SiCF 2H, to provide difluoromethylated isoxazolines in good yields. Conjugated styryl-4-nitroisoxazoles were also nicely converted into the corresponding CF 2H 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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          Most cited references 36

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          Fluorination in Medicinal Chemistry: Methods, Strategies, and Recent Developments

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            Hydrogen Bond Donor Properties of the Difluoromethyl Group

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              ENZYMES AT WORK

               ANN M. THAYER (2006)
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                Author and article information

                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
                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.

                Article
                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 .

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