二氢-3-（三苯基磷亚基）-2,5-噻吩二酮：一种通过硫代酸中间体方便地合成取代的1,4-硫氮杂卓-5-酮和哌啶酮的合成子。
Dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione: A Convenient Synthon for the Preparation of Substituted 1,4-Thiazepin-5-ones and Piperidinones via the Intermediacy of Thioacids.
作者信息
Crich David, Rahaman Md Yeajur
机构信息
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
出版信息
Tetrahedron. 2010 Aug 14;66(33):6383-6390. doi: 10.1016/j.tet.2010.04.002.
Abstract
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.
摘要
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。
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本文引用的文献
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Preparation and reactions of N-thioformyl peptides from amino thioacids and isonitriles.由氨基硫代酸和异腈制备N-硫甲酰基肽及其反应
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Coupling reactions of hindered isonitriles and hindered alkyl thioacids: Mechanistic studies.受阻异腈与受阻烷基硫代酸的偶联反应：机理研究。
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