N-(Trimethylsilyl)-2-amino-5-nitrothiazole: An Efficient Reagent for the Direct Synthesis of 2-Amino-5-nitrothiazole-Based Antimicrobial Agents
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Date
2022-11
Journal Title
Journal ISSN
Volume Title
Publisher
Georg Thieme Verlag KG
Abstract
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.
Description
This is the accepted manuscript version of an article published by Georg Thieme Verlag [N-(Trimethylsilyl)-2-amino-5-nitrothiazole: An Efficient Reagent for the Direct Synthesis of 2-Amino-5-nitrothiazole-Based Antimicrobial Agents. Synlett 34, 02 p173-175 (2022)] https://doi.org/10.1055/s-0042-1752343
Keywords
2-amino-5-nitrothiazole, N-silylation, antimicrobials, antiviral, biofilms
Citation
Koenig, H. N., Demeritte, A. R., Livinghouse, T., & Nelson, G. P. (2023). N-(Trimethylsilyl)-2-amino-5-nitrothiazole: An Efficient Reagent for the Direct Synthesis of 2-Amino-5-nitrothiazole-Based Antimicrobial Agents. Synlett, 34(02), 173-175.