Department of Chemistry, North Carolina State University , Raleigh, North Carolina 27695, United States.
Org Lett. 2015 Sep 18;17(18):4542-5. doi: 10.1021/acs.orglett.5b02256. Epub 2015 Sep 2.
An oxidative formation of 1,4,2-oxathiazoles from readily available thiohydroximic acids is reported. A variety of alkyl, aryl, and heteroaryl substituents are well tolerated for both the thiohydroximic acid and activating fragments, and the reaction has been demonstrated on gram-scale. This reaction represents the only method currently available to prepare a diverse set of oxathiazoles and expands the chemistry of C-H oxidation via appended N-OH functional groups. Finally, we also demonstrate the rapid preparation of a 1,4,2-oxathiazole analog of an anticancer lead molecule.
本文报道了一种从易得的硫代羟肟酸出发，经氧化合成 1,4,2-噁噻唑的方法。该反应对硫代羟肟酸和活化片段中的各种烷基、芳基和杂芳基取代基都具有良好的耐受性，并且已经在克级规模上进行了验证。该反应代表了目前制备各种噁噻唑的唯一方法，并通过附加的 N-OH 官能团扩展了 C-H 氧化化学。最后，我们还展示了一种抗癌先导分子的 1,4,2-噁噻唑类似物的快速制备方法。
