治疗剂的良性合成:球磨机中不对称1,4-二芳基-1,4-二氢吡啶的多米诺骨牌合成

IF 5.8 3区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Green Chemistry Letters and Reviews Pub Date : 2022-10-02 DOI:10.1080/17518253.2022.2129464

C. Blázquez-Barbadillo, Juan F González, A. Porcheddu, D. Virieux, J. Menéndez, E. Colacino

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引用次数: 4

摘要

研究了球磨法制备不对称n -芳基-5,6-未取代-1,4-二氢吡啶(DHPs)的方法。研究了三种不同的机械化学多米诺骨牌反应(一锅/一步或逐步)，对任何机械化学过程的工艺参数进行了调节，并揭示了与基于溶液的机械化学途径的差异。选择最合适的方法是由反应物和中间体的物理状态驱动的，而最终的1,4- dhp的物理状态指导催化剂的选择(Lewis vs Brønsted)和回收最终产物的后处理类型(柱层析vs水中沉淀)。本文所描述的结果在合成方法领域是前所未有的，以获得不同取代的1,4- dhps，这是一种与合成和药用用途相关的n -杂环支架。图形抽象

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Benign synthesis of therapeutic agents: domino synthesis of unsymmetrical 1,4-diaryl-1,4-dihydropyridines in the ball-mill

ABSTRACT The solvent-free preparation of unsymmetrical N-aryl-5,6-unsubstituted-1,4-dihydropyridines (DHPs) by ball-milling was investigated. Three different mechanochemical domino reactions (one-pot/one step or stepwise) were studied, the process parameters underlying any mechanochemical process were modulated and the differences with solution-based mechanistic pathways were disclosed. The selection of the most suitable method was driven by the physical state of both the reactants and the intermediates, while the physical state of the final 1,4-DHP directed the choice of the catalyst (Lewis vs Brønsted) and the type of work-up to recover the final products (by column chromatography vs precipitation in water). The results herein described are unprecedented in the arena of synthetic methods to access diversely substituted 1,4-DHPs, an N-heterocyclic scaffold relevant to both synthetic and medicinal purposes. GRAPHICAL ABSTRACT

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来源期刊

Green Chemistry Letters and Reviews CHEMISTRY, MULTIDISCIPLINARY-GREEN & SUSTAINABLE SCIENCE & TECHNOLOGY

CiteScore

9.10

自引率

3.00%

发文量

期刊介绍： Green Chemistry Letters and Reviews is an Open Access, peer-reviewed journal focused on rapid publication of innovative new syntheses and procedures that reduce or eliminate the use and generation of hazardous materials. Reviews of state-of-the-art green chemistry technologies are also included within the journal''s scope. Green Chemistry Letters and Reviews is divided into three overlapping topic areas: research, education, and industrial implementation. The journal publishes both letters, which concisely communicate the most time-sensitive results, and reviews, which aid researchers in understanding the state of science on important green chemistry topics. Submissions are encouraged which apply the 12 principles of green chemistry to: -Green Chemistry Education- Synthetic Reaction Pathways- Research and Process Analytical Techniques- Separation and Purification Technologies- Renewable Feedstocks- Degradable Products