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无金属和氧化剂温和条件下碱促进的烯胺酮碳-碳双键断裂合成NH2-结构脒类化合物

本站小编 Free考研考试/2022-02-14

摘要/Abstract



报道了室温条件下烯胺酮和磺酰叠氮通过碳-碳双键断裂合成N-磺酰基醚类化合物的方法.反应在1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)存在下进行,无需使用任何金属和氧化剂,具有良好的底物适用性.烯胺酮上的15N同位素标记实验证实,磺酰叠氮仅作为产物中的磺酰胺片段供体,同时,该实验也有力地支持反应机理涉及关键的1,2,3-三唑啉中间体的原位形成以及环分解.
关键词: 烯胺酮, 碳-碳双键断裂, 无金属, 无氧化剂,
The C=C double bond cleavage of NH2-functionalized enaminones has been realized at room temperature to provide various N-sulfonyl amidines by reacting with sulfonyl azides. The reactions take place with good substrate tolerance in the presence of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) without any metal or oxidant reagent. The 15N-labelling experiment on enaminone indicates that the sulfonyl azide component donates solely the sulfonamide fragment, and the reaction mechanism involving a key decomposition of the in situ generated 1,2,3-triazoline intermediate is convictively supported.
Key words: Enaminone, C=C bond cleavage, Metal-free, Oxidant-free, Amidines


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