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
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Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00095