A Cascade Markovnikov Addition / Lewis Acid-Catalyzed Rearrangement of Methyleneaziridines and Carboxylic Acids: Continuous-Flow Synthesis of α-Amidoketones

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-04-25 DOI:10.1039/d5qo00495k

Bin Pan, Haotian Sun, Feng Li, Qing-Bao Zhang, Shanshan Zhang, Jia-Hao Wang, Meng-Rui Xu, Jing-Tian Ge, Zi-Qing Hu, Shang Lv, Lijuan Feng, Guofu Huang

引用次数: 0

Abstract

α-Amidoketones are essential structural motifs in pharmaceuticals and synthetic chemistry. In this study, we describe a novel synthetic method that involves a cascade addition reaction, followed by a Lewis acid-catalyzed rearrangement of methyleneaziridines and carboxylic acids. Additionally, we developed a high-speed continuous flow synthesis method, allowing the reaction to proceed efficiently within 3.5 minutes. The incorporation of a greener silica gel-packed catalyzed column in this continuous flow system effectively facilitates the rearrangement step, providing a more environmentally friendly approach for synthesizing α-amidoketone compounds.

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级联Markovnikov加成/ Lewis酸催化的亚甲叠氮嘧啶和羧酸重排：α-氨基酮的连续流合成

α-氨基酮是药物和合成化学中必不可少的结构基序。在这项研究中，我们描述了一种新的合成方法，该方法涉及级联加成反应，随后是刘易斯酸催化的亚甲基亚氮吡啶和羧酸的重排。此外，我们开发了一种高速连续流合成方法，使反应在3.5分钟内有效地进行。在这个连续流系统中加入了一个更环保的硅胶填充催化柱，有效地促进了重排步骤，为合成α-酰胺酮化合物提供了更环保的方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.