Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities

The acceptorless dehydrogenative coupling (ADC) reaction is an efficient method for synthesizing quinoline and its derivatives. In this paper, various substituted quinolines were synthesized from 2-aminobenzyl alcohols and aryl/heteroaryl/alkyl secondary alcohols in one pot via a cyclometalated irid...

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Main Authors: Hongling Shui, Yuhong Zhong, Renshi Luo, Zhanyi Zhang, Jiuzhong Huang, Ping Yang, Nianhua Luo
Format: Article
Language:English
Published: Beilstein-Institut 2022-10-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.18.159
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author Hongling Shui
Yuhong Zhong
Renshi Luo
Zhanyi Zhang
Jiuzhong Huang
Ping Yang
Nianhua Luo
author_facet Hongling Shui
Yuhong Zhong
Renshi Luo
Zhanyi Zhang
Jiuzhong Huang
Ping Yang
Nianhua Luo
author_sort Hongling Shui
collection DOAJ
description The acceptorless dehydrogenative coupling (ADC) reaction is an efficient method for synthesizing quinoline and its derivatives. In this paper, various substituted quinolines were synthesized from 2-aminobenzyl alcohols and aryl/heteroaryl/alkyl secondary alcohols in one pot via a cyclometalated iridium-catalyzed ADC reaction. This method has some advantages, such as easy availability of raw materials, mild reaction conditions, wide range of substrates, and environmental friendliness which conforms to the principles of green chemistry. Furthermore, a gram-scale experiment with low catalyst loading offers the potential to access the aryl/heteroaryl quinolones in suitable amounts. In addition, the antibacterial and antifungal activities of the synthesized quinolines were evaluated in vitro, and the experimental results showed that the antibacterial activities of compounds 3ab, 3ad, and 3ah against Gram-positive bacteria and compound 3ck against C. albicans were better than the reference drug norfloxacin.
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spelling doaj.art-8c25895071bd40c183117c6b9cd39e652022-12-22T02:40:22ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-10-011811507151710.3762/bjoc.18.1591860-5397-18-159Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activitiesHongling Shui0Yuhong Zhong1Renshi Luo2Zhanyi Zhang3Jiuzhong Huang4Ping Yang5Nianhua Luo6School of Pharmacy, Gannan Medical University, Ganzhou, 341000, Jiangxi Province, P. R. China School of Pharmacy, Gannan Medical University, Ganzhou, 341000, Jiangxi Province, P. R. China School of Pharmacy, Gannan Medical University, Ganzhou, 341000, Jiangxi Province, P. R. China School of Pharmacy, Gannan Medical University, Ganzhou, 341000, Jiangxi Province, P. R. China School of Pharmacy, Gannan Medical University, Ganzhou, 341000, Jiangxi Province, P. R. China Institute of Microbiology, Guangdong Academy of Sciences, Guangzhou 510070, P. R. China School of Pharmacy, Gannan Medical University, Ganzhou, 341000, Jiangxi Province, P. R. China The acceptorless dehydrogenative coupling (ADC) reaction is an efficient method for synthesizing quinoline and its derivatives. In this paper, various substituted quinolines were synthesized from 2-aminobenzyl alcohols and aryl/heteroaryl/alkyl secondary alcohols in one pot via a cyclometalated iridium-catalyzed ADC reaction. This method has some advantages, such as easy availability of raw materials, mild reaction conditions, wide range of substrates, and environmental friendliness which conforms to the principles of green chemistry. Furthermore, a gram-scale experiment with low catalyst loading offers the potential to access the aryl/heteroaryl quinolones in suitable amounts. In addition, the antibacterial and antifungal activities of the synthesized quinolines were evaluated in vitro, and the experimental results showed that the antibacterial activities of compounds 3ab, 3ad, and 3ah against Gram-positive bacteria and compound 3ck against C. albicans were better than the reference drug norfloxacin.https://doi.org/10.3762/bjoc.18.159acceptorless dehydrogenative coupling reactionantibacterialcyclometalated iridium complexesquinolines
spellingShingle Hongling Shui
Yuhong Zhong
Renshi Luo
Zhanyi Zhang
Jiuzhong Huang
Ping Yang
Nianhua Luo
Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities
Beilstein Journal of Organic Chemistry
acceptorless dehydrogenative coupling reaction
antibacterial
cyclometalated iridium complexes
quinolines
title Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities
title_full Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities
title_fullStr Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities
title_full_unstemmed Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities
title_short Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities
title_sort cyclometalated iridium complexes catalyzed acceptorless dehydrogenative coupling reaction construction of quinoline derivatives and evaluation of their antimicrobial activities
topic acceptorless dehydrogenative coupling reaction
antibacterial
cyclometalated iridium complexes
quinolines
url https://doi.org/10.3762/bjoc.18.159
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