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-TSA·HO催化由芳胺、芳基乙炔和二甲基亚砜无金属且环境友好地合成4-芳基喹啉。

-TSA·HO catalyzed metal-free and environmentally benign synthesis of 4-aryl quinolines from arylamine, arylacetylene, and dimethyl sulfoxide.

作者信息

Faraz Simra, Khan Abu Taleb

机构信息

Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, India.

出版信息

Org Biomol Chem. 2023 Sep 27;21(37):7553-7560. doi: 10.1039/d3ob00993a.

Abstract

An environmentally benign and metal-free synthesis of 4-aryl quinolines is reported by employing readily available arylamine, arylacetylene, and DMSO in the presence of 20 mol% -TSA·HO. In the present protocol, the solvent DMSO serves as a reactant cum solvent for providing the C2 carbon atom of the quinoline skeleton. Notably, the reaction proceeds effectively and efficiently without the involvement of any metal catalyst, ligand, and co-catalyst as additives and inert atmospheric reaction conditions. This method provides high atom economy and good yields, and two - and one - bonds are formed in a single step through a three-component reaction.

摘要

报道了一种环境友好且无金属的4-芳基喹啉合成方法,该方法使用易得的芳胺、芳基乙炔和二甲基亚砜,在20 mol%的对甲苯磺酸一水合物存在下进行反应。在本方法中,溶剂二甲基亚砜既作为反应物又作为溶剂,用于提供喹啉骨架的C2碳原子。值得注意的是,该反应在不涉及任何金属催化剂、配体和助催化剂作为添加剂以及惰性气氛反应条件下有效地进行。此方法具有高原子经济性和良好的产率,通过三组分反应一步形成两根和一根化学键。

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Utilization of DMSO as a solvent-cum-reactant: synthesis of fused 2-aryl-4-methylquinolines.
Org Biomol Chem. 2024 Jul 10;22(27):5608-5617. doi: 10.1039/d4ob00938j.

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