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使用多种催化剂的克劳森-卡斯吡咯合成法:从传统方法到更绿色方法的转变

Clauson-Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach.

作者信息

Singh Dileep Kumar, Kumar Rajesh

机构信息

Department of Chemistry, Bipin Bihari College, Affiliated to Bundelkhand University, Jhansi-284001, Uttar Pradesh, India.

P.G. Department of Chemistry, R. D. S. College, B. R. A. Bihar University, Muzaffarpur-842002, Bihar, India.

出版信息

Beilstein J Org Chem. 2023 Jun 27;19:928-955. doi: 10.3762/bjoc.19.71. eCollection 2023.

Abstract

Pyrrole is an important aromatic heterocyclic scaffold found in many natural products and predominantly used in pharmaceuticals. Continuous efforts are being made to design and synthesize various pyrrole derivatives using different synthetic procedures. Among them, the Clauson-Kaas reaction is a very old and well-known method for synthesizing a large number of N-substituted pyrroles. In recent years, due to global warming and environmental concern, research laboratories and pharmaceutical industries around the world are searching for more environmentally friendly reaction conditions for synthesizing compounds. As a result, this review describes the use of various eco-friendly greener protocols to synthesize N-substituted pyrroles. This synthesis involves the reaction of various aliphatic/aromatic primary amines, and sulfonyl primary amines with 2,5-dimethoxytetrahydrofuran in the presence of numerous acid catalysts and transition metal catalysts. The goal of this review is to summarize the synthesis of various N-substituted pyrrole derivatives using a modified Clauson-Kaas reaction under diverse conventional and greener reaction conditions.

摘要

吡咯是一种重要的芳香杂环骨架,存在于许多天然产物中,主要用于制药领域。人们一直在不断努力,使用不同的合成方法来设计和合成各种吡咯衍生物。其中,克劳森 - 卡斯反应是一种非常古老且著名的合成大量N - 取代吡咯的方法。近年来,由于全球变暖和环境问题,世界各地的研究实验室和制药行业都在寻找更环保的反应条件来合成化合物。因此,本综述描述了使用各种环保的绿色方法合成N - 取代吡咯。这种合成涉及各种脂肪族/芳香族伯胺以及磺酰基伯胺与2,5 - 二甲氧基四氢呋喃在多种酸催化剂和过渡金属催化剂存在下的反应。本综述的目的是总结在不同的传统和绿色反应条件下,使用改进的克劳森 - 卡斯反应合成各种N - 取代吡咯衍生物的方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10ae/10315892/49fc1b23ea06/Beilstein_J_Org_Chem-19-928-g002.jpg

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