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Batch vs Continuous‐Flow Method to Synthesize N‐(3‐acylamidopropyl)lactams through N‐C Bond Cleavage in Amides with Amidines
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2024-11-02 , DOI: 10.1002/adsc.202401179 Karthick Govindan, Chen Nian-Qi, Gokulakannan Venkatachalam, Tsz Fai Leung, Wei-Yu Lin
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2024-11-02 , DOI: 10.1002/adsc.202401179 Karthick Govindan, Chen Nian-Qi, Gokulakannan Venkatachalam, Tsz Fai Leung, Wei-Yu Lin
The selective N‐C bond cleavage of amides to create value‐added products through a transition metal‐free approach has become a significant challenge. Here, we present a method to convert amides into N‐(3‐acylamidopropyl)lactams through sequential amide chemoselective N‐C bond cleavage and amidine ring opening under mild conditions, applicable in batch and continuous flow processes. These methods utilize bench‐stable reagents and are operationally straightforward and mild, enabling synthesis on a gram scale with excellent functional group tolerance. Additionally, the synthetic feasibility of these reactions under flow conditions has proven to be highly efficient, providing N‐(3‐acylamidopropyl)lactam derivatives with improved yields and shorter reaction time.
中文翻译:
在酰胺与脒的酰胺中通过 N-C 键裂解合成 N-(3-酰基酰胺丙基)内酰胺的批量与连续流法
酰胺的选择性 N-C 键裂解以通过无过渡金属方法创造增值产品已成为一项重大挑战。在这里,我们提出了一种在温和条件下通过连续酰胺化学选择性 N-C 键裂解和脒环开裂将酰胺转化为 N-(3-酰基酰胺丙基)内酰胺的方法,适用于间歇和连续流工艺。这些方法使用工作台稳定的试剂,操作简单且温和,能够在克级上合成,具有出色的官能团耐受性。此外,这些反应在流动条件下的合成可行性已被证明是高效的,为N-(3-酰基酰胺丙基)内酰胺衍生物提供了更高的产率和更短的反应时间。
更新日期:2024-11-02
中文翻译:
在酰胺与脒的酰胺中通过 N-C 键裂解合成 N-(3-酰基酰胺丙基)内酰胺的批量与连续流法
酰胺的选择性 N-C 键裂解以通过无过渡金属方法创造增值产品已成为一项重大挑战。在这里,我们提出了一种在温和条件下通过连续酰胺化学选择性 N-C 键裂解和脒环开裂将酰胺转化为 N-(3-酰基酰胺丙基)内酰胺的方法,适用于间歇和连续流工艺。这些方法使用工作台稳定的试剂,操作简单且温和,能够在克级上合成,具有出色的官能团耐受性。此外,这些反应在流动条件下的合成可行性已被证明是高效的,为N-(3-酰基酰胺丙基)内酰胺衍生物提供了更高的产率和更短的反应时间。