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铁催化2-氨基苯乙烯与醇和甲基芳烃的氧化环化反应合成多取代喹啉

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

作者信息

Lee Seok Beom, Chun Simin, Choi Seung Hyun, Hong Junhwa, Oh Dong-Chan, Hong Suckchang

机构信息

Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.

Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.

出版信息

J Org Chem. 2023 Jul 7;88(13):8099-8113. doi: 10.1021/acs.joc.3c00095. Epub 2023 Jun 7.

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--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.

摘要

在此,我们展示了铁催化醇/甲基芳烃与2-氨基苯乙烯的氧化环化反应以合成多取代喹啉。在铁催化剂和二叔丁基过氧化物存在下,醇和甲基芳烃等低氧化态底物被转化为醛。然后,通过亚胺缩合/自由基环化/氧化芳构化反应合成喹啉骨架。我们的方法具有广泛的底物范围,喹啉产物的各种功能化和荧光应用证明了其合成能力。

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