Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC.
Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 80708, Taiwan, ROC.
Org Lett. 2021 Mar 5;23(5):1600-1605. doi: 10.1021/acs.orglett.1c00010. Epub 2021 Feb 11.
A LiOH-promoted hydrolysis selective C-N cleavage of twisted -acyl glutarimide for the synthesis of primary amides under mild conditions has been developed. The reaction is triggered by a ring opening of glutarimide followed by C-N cleavage to afford primary amides using 2 equiv of LiOH as the base at room temperature. The efficacy of the reactions was considered and administrated for various aryl and alkyl substituents in good yield with high selectivity. Moreover, gram-scale synthesis of primary amides using a continuous flow method was achieved. It is noted that our new methodology can apply under both batch and flow conditions for synthetic and industrial applications.
已开发出一种在温和条件下通过扭曲的酰基戊二酰亚胺的 LiOH 促进水解选择性 C-N 裂解来合成伯酰胺的方法。该反应是通过戊二酰亚胺开环引发的，然后在室温下使用 2 当量的 LiOH 作为碱进行 C-N 裂解，从而得到伯酰胺。考虑了反应的功效，并在良好的收率和高选择性下对各种芳基和烷基取代基进行了处理。此外，还通过连续流动法实现了伯酰胺的克级合成。值得注意的是，我们的新方法可在间歇和流动条件下应用于合成和工业应用。
