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铁氮位点和铁纳米颗粒协同催化用于高效合成喹啉和喹唑啉酮——胺与醛的氧化偶联反应

Synergistic catalysis on Fe-N sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones oxidative coupling of amines and aldehydes.

作者信息

Ma Zhiming, Song Tao, Yuan Youzhu, Yang Yong

机构信息

Qingdao Institute of Bioenergy and Bioprocess Technology , Chinese Academy of Sciences , Qingdao 266101 , P. R. China.

University of Chinese Academy of Sciences , Beijing , 100049 , P. R. China.

出版信息

Chem Sci. 2019 Sep 23;10(44):10283-10289. doi: 10.1039/c9sc04060a. eCollection 2019 Nov 28.

DOI:10.1039/c9sc04060a
PMID:32110314
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6984390/
Abstract

In this paper, we developed a reusable heterogeneous non-precious iron nanocomposite comprising metallic Fe-FeC nanoparticles and Fe-N sites on N-doped porous carbon, which allows for highly efficient synthesis of quinolines and quinazolinones oxidative coupling of amines and aldehydes using HO as the oxidant in aqueous solution under mild conditions. A set of quinazolines and quinazolinones were synthesized in high yields with a broad substrate scope and good tolerance of functional groups. Characterization and control experiments disclose that a synergistic effect between the metallic Fe nanoparticles and built-in Fe-N sites is primarily responsible for the outstanding catalytic performance. Furthermore, the iron nanocomposite could be readily recovered for successive use without appreciable loss in catalytic activity and selectivity. This work provides an expedient and sustainable method to access pharmaceutically relevant N-heterocycles.

摘要

在本文中,我们开发了一种可重复使用的多相非贵金属铁纳米复合材料,其由金属Fe-FeC纳米颗粒和氮掺杂多孔碳上的Fe-N位点组成,该复合材料能够在温和条件下,以水为溶剂,H₂O为氧化剂,高效合成喹啉和喹唑啉酮,通过胺和醛的氧化偶联反应,一系列喹唑啉和喹唑啉酮得以高产率合成,底物范围广,官能团耐受性好。表征和对照实验表明,金属铁纳米颗粒与内置Fe-N位点之间的协同效应是其出色催化性能的主要原因。此外,铁纳米复合材料可以很容易地回收并连续使用,而催化活性和选择性没有明显损失。这项工作提供了一种便捷且可持续的方法来获得与药物相关的氮杂环化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad8c/6984390/a12114dd935a/c9sc04060a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad8c/6984390/1b8e25abb7d2/c9sc04060a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad8c/6984390/82a0577fa72e/c9sc04060a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad8c/6984390/2df46a22ce13/c9sc04060a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad8c/6984390/345c46b0ba73/c9sc04060a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad8c/6984390/a12114dd935a/c9sc04060a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad8c/6984390/1b8e25abb7d2/c9sc04060a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad8c/6984390/82a0577fa72e/c9sc04060a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad8c/6984390/2df46a22ce13/c9sc04060a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad8c/6984390/345c46b0ba73/c9sc04060a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad8c/6984390/a12114dd935a/c9sc04060a-s2.jpg

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2
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Chempluschem. 2017 Jan;82(1):136-143. doi: 10.1002/cplu.201600460. Epub 2016 Oct 31.
3
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