Lei Xiaofang, Wang Yuanyuan, Fan Erkang, Sun Zhihua
College of Chemistry and Chemical Engineering , Shanghai University of Engineering Science 333 Longteng Road , Shanghai 201620 , China.
Department of Biochemistry , University of Washington , 1705 NE Pacific Street , Seattle , Washington 98195 , United States.
Org Lett. 2019 Mar 1;21(5):1484-1487. doi: 10.1021/acs.orglett.9b00275. Epub 2019 Feb 11.
Activation of disulfides with N-halogen succinimide in the presence of TEMPO allows insertion reaction by an isocyanide, the product of which can further accept a wide range of nucleophiles for the generation of isothioureas and related molecular moieties. This new procedure overcomes previous methods that accept essentially only aryl amines as the third nucleophilic component. The diverse nucleophiles usable in our new protocol make this approach a general method for de novo synthesis of many S-containing heterocycles.
在TEMPO存在下，用N-卤代琥珀酰亚胺活化二硫化物，可使异腈发生插入反应，其产物可进一步接受多种亲核试剂以生成异硫脲和相关分子片段。这一新方法克服了以往基本上只接受芳基胺作为第三亲核组分的方法。我们新方案中可用的多种亲核试剂使该方法成为从头合成许多含硫杂环的通用方法。
