Iron-Catalyzed Oxidative Cyclization of 2‑Amino Styrenes with Alcohols and Methyl Arenes for the Synthesis of Polysubstituted Quinolines

Herein, we present the iron-catalyzed oxidative cyclization of alcohol/methyl arene with 2-amino styrene to synthesize polysubstituted quinoline. Low-oxidation level substrates such as alcohols and methyl arenes are converted to aldehydes in the presence of an iron catalyst and di-t-butyl peroxide....

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Veröffentlicht in:	Journal of organic chemistry 2023-07, Vol.88 (13), p.8099-8113
Hauptverfasser:	Lee, Seok Beom, Chun, Simin, Choi, Seung Hyun, Hong, Junhwa, Oh, Dong-Chan, Hong, Suckchang
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols Catalysis Cyclization Iron Oxidative Stress Quinolines Styrenes
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container_end_page	8113
container_issue	13
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container_title	Journal of organic chemistry
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creator	Lee, Seok Beom Chun, Simin Choi, Seung Hyun Hong, Junhwa Oh, Dong-Chan Hong, Suckchang
description	Herein, we present the iron-catalyzed oxidative cyclization of alcohol/methyl arene with 2-amino styrene to synthesize polysubstituted quinoline. Low-oxidation level substrates such as alcohols and methyl arenes are converted to aldehydes in the presence of an iron catalyst and di-t-butyl peroxide. Then, the quinoline scaffold is synthesized through imine condensation/radical cyclization/oxidative aromatization. Our protocol showed a broad substrate scope, and various functionalization and fluorescence applications of quinoline products demonstrated its synthetic ability.
doi_str_mv	10.1021/acs.joc.3c00095
format	Article
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Org. Chem</addtitle><date>2023-07-07</date><risdate>2023</risdate><volume>88</volume><issue>13</issue><spage>8099</spage><epage>8113</epage><pages>8099-8113</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Herein, we present the iron-catalyzed oxidative cyclization of alcohol/methyl arene with 2-amino styrene to synthesize polysubstituted quinoline. Low-oxidation level substrates such as alcohols and methyl arenes are converted to aldehydes in the presence of an iron catalyst and di-t-butyl peroxide. Then, the quinoline scaffold is synthesized through imine condensation/radical cyclization/oxidative aromatization. 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subjects	Alcohols Catalysis Cyclization Iron Oxidative Stress Quinolines Styrenes
title	Iron-Catalyzed Oxidative Cyclization of 2‑Amino Styrenes with Alcohols and Methyl Arenes for the Synthesis of Polysubstituted Quinolines
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