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苯醌配体促进的钌催化2-氨基芳基醛和酮与支链胺的脱氨基偶联反应用于区域选择性合成喹啉衍生物

Benzoquinone Ligand-Enabled Ruthenium-Catalyzed Deaminative Coupling of 2-Aminoaryl Aldehydes and Ketones with Branched Amines for Regioselective Synthesis of Quinoline Derivatives.

作者信息

Gnyawali Krishna Prasad, Shakenov Aldiyar, Kirinde Arachchige Pandula T, Yi Chae S

机构信息

Department of Chemistry, Marquette University, Milwaukee, Wisconsin 53233, United States.

出版信息

J Org Chem. 2024 Aug 16;89(16):11119-11135. doi: 10.1021/acs.joc.4c00063. Epub 2024 Jul 26.

DOI:10.1021/acs.joc.4c00063
PMID:39058560
Abstract

The catalytic system generated from the cationic Ru-H complex [(CH)(PCy)(CO)RuH]BF () with 2,3,4,5-tetrachloro-1,2-benzoquinone () was found to be highly effective for promoting the deaminative coupling reaction of 2-aminoaryl aldehydes with branched amines to form 2-substituted quinoline products. The analogous deaminative coupling reaction of 2-aminoaryl ketones with branched amines led to the regioselective formation of 2,4-disubstituted quinoline products. A number of biologically active quinoline derivatives including graveolinine and a triplex DNA intercalator have been synthesized by using the catalytic method.

摘要

由阳离子钌氢配合物[(CH)(PCy)(CO)RuH]BF()与2,3,4,5-四氯-1,2-苯醌()生成的催化体系被发现对促进2-氨基芳基醛与支链胺的脱氨基偶联反应以形成2-取代喹啉产物非常有效。2-氨基芳基酮与支链胺的类似脱氨基偶联反应导致区域选择性地形成2,4-二取代喹啉产物。通过使用该催化方法已经合成了许多具有生物活性的喹啉衍生物,包括graveolinine和一种三链DNA嵌入剂。

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