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使用低熔点深共熔混合物快速高效合成取代吡咯。

An expeditious and highly efficient synthesis of substituted pyrroles using a low melting deep eutectic mixture.

机构信息

Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, Okhla, New Delhi, 110025, India.

出版信息

Org Biomol Chem. 2021 Nov 18;19(44):9732-9745. doi: 10.1039/d1ob01618k.

Abstract

An expeditious green method for the synthesis of diverse valued substituted pyrroles through a Paal-Knorr condensation reaction, using a variety of amines and 2,5-hexanedione/2,5-dimethoxytetrahydrofuran in the presence of a low melting mixture of ,-dimethylurea and -(+)-tartaric acid (which acts as a dual catalyst/solvent system), has fruitfully been revealed. Herein, we have disclosed the applicability of this simple yet effective strategy for the generation of mono- and dipyrroles in good to excellent yields. Moreover, -symmetric tripyrrolo-truxene derivatives have also been assembled by means of cyclotrimerization, Paal-Knorr and Clauson-Kaas reactions as crucial steps. Interestingly, the melting mixture was recovered and reused with only a gradual decrease in the catalytic activity (over four cycles) without any significant drop in the yield of the product. This particular methodology is simple, rapid, environmental friendly, and high yielding for the generation of a variety of pyrroles. To the best of our knowledge, the present work reveals the fastest greener method reported up to this date for the construction of substituted pyrroles by utilizing the Paal-Knorr synthetic protocol, achieving impressive yields under operationally simple reaction conditions without involving any precarious/dangerous catalysts or unsafe volatile organic solvents.

摘要

一种通过 Paal-Knorr 缩合反应,使用各种胺和 2,5-己二酮/2,5-二甲氧基四氢呋喃,在低熔点混合的,-二甲基脲和 -(+)-酒石酸(作为双催化剂/溶剂体系)的存在下,快速合成各种取代的吡咯的绿色方法已经得到了充分的揭示。在这里,我们已经展示了这种简单而有效的策略在生成单和二吡咯方面的适用性,产率良好到优秀。此外,通过环三聚化、Paal-Knorr 和 Clauson-Kaas 反应作为关键步骤,还组装了 -对称的三吡咯并三嗪衍生物。有趣的是,熔融混合物被回收并重复使用,仅在催化活性(超过四个循环)逐渐下降的情况下,而产物的产率没有明显下降。这种特殊的方法简单、快速、环保,并且可以高产率地生成各种吡咯。据我们所知,本工作揭示了迄今为止利用 Paal-Knorr 合成方案构建取代吡咯的最快的绿色方法,在不涉及任何不稳定/危险催化剂或不安全挥发性有机溶剂的操作简单的反应条件下,实现了令人印象深刻的产率。

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