Departamento de Química Orgánica, Cátedra de Química Farmacéutica, Universidad de la República (UdelaR) , Avda. General Flores 2124, CC1157 Montevideo, Uruguay.
J Org Chem. 2014 Feb 21;79(4):1856-60. doi: 10.1021/jo402661b. Epub 2014 Feb 10.
Herein, we describe an approach toward selenazole preparation based on the cycloisomerization of propargyl selenoamides. The selenoamides were synthesized in situ using the Ishihara reagent with spontaneous cyclization to form the 2,5-disubstituted selenazoles. Heterocylcles 9a-j were prepared using readily available starting materials, and yields ranged from moderate to good (20-80%). Methylselenazole 9a could be transformed into a bromomethyl derivative 13 using NBS. The intermediate 13 would provide a more versatile building block for further derivatizations, e.g., the cyanide 14.
在此，我们描述了一种基于炔丙基硒酰胺环异构化制备硒唑的方法。硒酰胺是使用 Ishihara 试剂原位合成的，通过自发环化形成 2,5-二取代硒唑。使用易得的起始原料制备了杂环 9a-j，产率从中等到良好（20-80%）。甲基硒唑 9a 可以用 NBS 转化为溴甲基衍生物 13。中间体 13 为进一步衍生化提供了更具通用性的构建块，例如氰化物 14。
