A Sustainable Approach to Synthesize Tetra‐ and Penta‐Substituted Pyrroles Under Three‐Component One‐Pot Synthesis Using Novel Thiourea‐Derived Organocatalysts

IF 2.7 4区 化学 Q1 CHEMISTRY, ORGANIC
Asian Journal of Organic Chemistry Pub Date : 2026-04-01 Epub Date: 2026-04-29 DOI:10.1002/ajoc.70414
Rajeev Singh , Naseem Ahmed
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引用次数: 0

Abstract

An efficient, synthetically challenging tetra‐ and penta‐substituted pyrroles are reported under one‐ pot three‐component reactions using thiourea‐based organocatalysts under mild reaction conditions. This method is noteworthy for its inexpensive catalyst, easy reaction conditions, air atmosphere, excellent yields, and scalability. Generally, these molecules are synthesized under the Paal–Knorr reaction. However, our protocol offers low organocatalyst loading, catalyst recycling, high atom economy, and a wide functional group tolerance, with product yields up to 91%. The plausible mechanism indicates that H‐bonding between the organocatalyst and the starting materials facilitates the intramolecular Michael addition to afford the intermediate, which then leads to highly substituted pyrrole derivatives.
利用新型硫脲类有机催化剂在三组分一锅法合成四和五取代吡咯的可持续方法
在温和的反应条件下,使用硫脲基有机催化剂,在一锅三组分反应中,获得了一种高效的、具有合成挑战性的四取代吡咯和五取代吡咯。该方法催化剂价格低廉,反应条件简单,空气气氛好,产率高,具有可扩展性。一般来说,这些分子是在Paal-Knorr反应下合成的。然而,我们的方案提供低有机催化剂负载,催化剂回收,高原子经济性和广泛的官能团耐受性,产品收率高达91%。该机制表明,有机催化剂和起始物质之间的氢键促进了分子内的Michael加成反应,从而产生了高取代的吡咯衍生物。
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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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