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Synthesis of functionalized γ-lactams by a lewis acid catalyzed ketene formation/cyclization/claisen rearrangement sequence of 5,5-disubstituted Meldrum’s acid
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2022-04-30 , DOI: 10.1016/j.tetlet.2022.153816 Xiao-Wan Lin 1 , Mei Han 1 , Mei-Hua Shen 1 , Chi-Fan Zhu 1 , Hua-Dong Xu 1
中文翻译:
路易斯酸催化 5,5-二取代 Meldrum 酸的烯酮形成/环化/克莱森重排序列合成功能化 γ-内酰胺
更新日期:2022-04-30
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2022-04-30 , DOI: 10.1016/j.tetlet.2022.153816 Xiao-Wan Lin 1 , Mei Han 1 , Mei-Hua Shen 1 , Chi-Fan Zhu 1 , Hua-Dong Xu 1
Affiliation
A series of γ-lactams were synthesized by intramolecular aza-claisen rearrangement of ketenes using Meldrum’s acid as ketene precursor. Derivatives of Meldrum’s acid with tertiary ammonia structure were used as raw material, and the reaction was catalyzed by Lewis acid at high-temperature conditions under microwave. Ketene formation by losing acetone and CO2, cyclization and claisen rearrangement occurred in sequence to form the γ-lactams.
中文翻译:
路易斯酸催化 5,5-二取代 Meldrum 酸的烯酮形成/环化/克莱森重排序列合成功能化 γ-内酰胺
以Meldrum's酸为乙烯酮前体,通过乙烯酮的分子内氮杂克莱森重排合成了一系列γ-内酰胺。以具有叔氨结构的Meldrum酸衍生物为原料,在微波高温条件下用路易斯酸催化反应。通过失去丙酮和CO 2形成乙烯酮,环化和克莱森重排依次发生,形成γ-内酰胺。