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铜(II)催化乙炔基亚甲基环氨基甲酸酯与胺的反应:多取代吡咯的合成

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

作者信息

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

机构信息

School of Chemistry and Chemical Engineering/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003, China.

Université Paris-Saclay, CNRS, Institut de Chimie Moléculaire et des Matériaux d'Orsay91400 Orsay, France.

出版信息

Org Lett. 2024 Nov 1;26(43):9237-9243. doi: 10.1021/acs.orglett.4c03334. Epub 2024 Oct 18.

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.

摘要

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,与市售胺反应,直接合成多取代吡咯。在温和条件下,以可接受至良好的产率获得了多种多取代吡咯。该方法具有底物范围广、官能团耐受性高和操作简便的特点,因此能够实现后期功能化以及生物活性化合物的快速合成,包括结构复杂的上市药物和天然产物。此外,放大实验进一步突出了该合成方法的实用性。

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