Chemistry & Biochemistry

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The Department of Chemistry and Biochemistry offers research-oriented programs culminating in the Doctor of Philosophy degree. The faculty in the department have expertise over a broad range of specialty areas including synthesis, structure, spectroscopy, and mechanism. In each of these fields, the strength of the department has been recognized at the international level.

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Author: search.filters.author.Demeritte, Amethyst R.Subject: search.filters.subject.antiviral

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    N-(Trimethylsilyl)-2-amino-5-nitrothiazole: An Efficient Reagent for the Direct Synthesis of 2-Amino-5-nitrothiazole-Based Antimicrobial Agents
    (Georg Thieme Verlag KG, 2022-11) Livinghouse, Tom; Koenig, Heidi N.; Demeritte, Amethyst R.; Nelson, Genevieve P.
    Here we report the synthesis of a novel reagent designed to prepare 2-amino-5-nitrothiazole (ANT) amides and analogues in high yields. N-(Trimethylsilyl)-2-amino-5-nitrothiazole (N-(TMS)-ANT) was prepared in 99% yield via silylation of ANT using 1,1,1,3,3,3-hexamethyldisilazane (HMDS), trimethylsilyl chloride (TMSCl), and catalytic saccharin. N-(TMS)-ANT is a superb reagent for the preparation of ANT amides in excellent yields. Notably, cyclic anhydrides and base-sensitive acyl chlorides can be utilized with N-(TMS)-ANT to furnish ANT amides that are difficult to prepare by previously reported procedures.
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