Cu(II)-Catalyzed Reaction of Ethynyl Methylene Cyclic Carbamates and Amines: Synthesis of Polysubstituted Pyrroles

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-10-18 DOI:10.1021/acs.orglett.4c03334

Yujie Zhao, Zhifei Zhao, Shijie Zhu, Shi-Wu Li, Liangjian Hu

引用次数: 0

Abstract

A copper-catalyzed efficient, operationally simple, general method for straightforward syntheses of polysubstituted pyrroles employing ethynyl methylene cyclic carbamates as precursors reacting with commercially available amines was first reported. A wide variety of polysubstituted pyrroles were obtained in acceptable to good yields under mild conditions. This protocol features broad substrate scope, high functional group tolerance, and easy operation, therefore enabling late-stage functionalization and rapid synthesis of bioactive compounds, including structurally complex marketed drugs and natural products. In addition, a scale-up experiment further highlighted the synthetic utility.

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Cu(II)-Catalyzed Reaction of Ethynyl Methylene Cyclic Carbamates and Amines：多取代吡咯的合成

首次报道了一种铜催化的高效、操作简单的通用方法，该方法以乙炔基亚甲基环氨基甲酸酯为前体，与市售胺发生反应，可直接合成多取代的吡咯。在温和的条件下，以可接受到良好的产率获得了多种多代吡咯。该方法具有底物范围广、官能团耐受性高、操作简便等特点，因此可以实现生物活性化合物的后期官能化和快速合成，包括结构复杂的上市药物和天然产物。此外，一项放大实验进一步凸显了该合成方法的实用性。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.