Crich David, Rahaman Md Yeajur
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Tetrahedron. 2010 Aug 14;66(33):6383-6390. doi: 10.1016/j.tet.2010.04.002.
Reaction of thiomaleic anhydride with triphenylphosphine gives the title compound which undergoes reaction with a variety of aldehydes to give a range of alkylidene thiomaleic anhydrides (substituted monothio itaconic anhydrides). Subsequent treatment with tert-butoxycarbonylamino-substituted thiols, or under radical conditions with tert-butoxycarbonylamino-substituted alkyl halides results in a series of substituted monothiomaleic anhydrides, that on exposure to trifluoroacetic acid and then base lead to thiocarboxyl substituted 1,4-thiazepin-5-ones and piperidinones, respectively, that are ultimately trapped by reaction with 2,4-dinitrobenzenesulfonamides to give the corresponding amides.
硫代马来酸酐与三苯基膦反应生成标题化合物，该化合物与多种醛反应生成一系列亚烷基硫代马来酸酐（取代的单硫代衣康酸酐）。随后用叔丁氧羰基氨基取代的硫醇处理，或在自由基条件下用叔丁氧羰基氨基取代的卤代烃处理，得到一系列取代的单硫代马来酸酐，这些化合物在暴露于三氟乙酸然后碱的条件下，分别生成硫代羧基取代的1,4 - 硫氮杂卓 - 5 - 酮和哌啶酮，最终通过与2,4 - 二硝基苯磺酰胺反应被捕获，得到相应的酰胺。
