Synonyms:Carbonothioate;Thiocarbonate;24389-08-0;DTXSID00570399;WRWHFVRDUAQRIQ-UHFFFAOYSA-L
Mamoru Shimizu and Mikiko Sodeoka presents a novel and efficient method for synthesizing carbamates, carbonates, and thiocarbonates using 1-alkoxycarbonyl-3-nitro-1,2,4-triazole (NT) transfer reagents. The study introduces stable crystalline reagents that react rapidly with amines, alcohols, and thiols to produce high-purity products without the need for additional bases or lengthy reaction times. The NT reagents, including Z-NT, Troc-NT, Fmoc-NT, and Teoc-NT, are synthesized from corresponding chloroformates and are shown to be highly stable and easy to handle. The reactions proceed quickly, often within minutes, and the byproduct NT can be easily removed by filtration, allowing for the isolation of pure carbamates without chromatographic purification. The method is particularly effective for the selective protection of nucleobases and the synthesis of various functionalized compounds that are challenging to produce using conventional methods. The study highlights the advantages of these new reagents, such as their stability, ease of handling, and the ability to recycle the byproduct NT, making them a practical and convenient alternative for the preparation of carbamates, carbonates, and thiocarbonates.
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