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可见光诱导的α,β-不饱和酸与胺及α-酮酸的脱羧环化反应用于合成2,4-二芳基喹啉

Visible-Light-Induced Decarboxylative Annulation of α,β-Unsaturated Acids with Amines and α-Keto Acids for 2,4-Diarylquinoline Synthesis.

作者信息

Das Suman, Maiti Souvik, Mondal Soumya, Mondal Subal, Midya Siba P, Ghosh Pradyut

机构信息

School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Kolkata, West Bengal 700032, India.

Department of Chemistry, Rammohan College, Kolkata, West Bengal 700009, India.

出版信息

Org Lett. 2025 Feb 14;27(6):1537-1543. doi: 10.1021/acs.orglett.5c00099. Epub 2025 Feb 3.

DOI:10.1021/acs.orglett.5c00099
PMID:39898463
Abstract

An efficient and sustainable approach for the synthesis of 2,4-diarylquinolines has been developed via a visible-light-promoted metal-free three-component decarboxylative annulation pathway. This one-pot protocol combines readily available feed-stock α,β-unsaturated acids, aromatic amines, and α-keto acids in a cascade manner to access substituted quinolines under eco-benign conditions. Moreover, mechanistic insights suggest initial C-C cross coupling followed by decarboxylative 6π electrocyclic annulation to afford the desired products. The broad substrates scope and excellent functional group tolerance make this protocol more attractive and synthetically applicable toward the construction of complex -heterocycles.

摘要

通过可见光促进的无金属三组分脱羧环化途径,开发了一种高效且可持续的合成2,4-二芳基喹啉的方法。该一锅法方案以级联方式将易于获得的原料α,β-不饱和酸、芳香胺和α-酮酸结合起来,在环境友好的条件下合成取代喹啉。此外,机理研究表明,首先进行C-C交叉偶联,然后进行脱羧6π电环化环化,以得到所需产物。广泛的底物范围和优异的官能团耐受性使该方案更具吸引力,并且在构建复杂杂环方面具有合成实用性。

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