Tetrahedron letters2022,Vol.997.DOI:10.1016/j.tetlet.2022.153847

A green and effective route leading to antiradical agents with 3-arylmethyl 4-hydroxyquinolin-2(1H)-one moiety

Mierina, Inese Stikute, Agnese
Tetrahedron letters2022,Vol.997.DOI:10.1016/j.tetlet.2022.153847

A green and effective route leading to antiradical agents with 3-arylmethyl 4-hydroxyquinolin-2(1H)-one moiety

Mierina, Inese 1Stikute, Agnese1
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作者信息

  • 1. Riga Tech Univ
  • 折叠

Abstract

A new, green, convenient, cost- and atom effective route leading to 3-arylmethyl 4-hydroxyquinolin-2 (1H)-ones from arylaldehydes and 1,3-dicarbonyl compounds in triethyl ammonium formate in good to excellent yield is presented. The provided method foresees the Knoevenagel condensation between a 4-hydroxyquinolin-2(1H)-one and an aromatic aldehyde followed by in situ trapping of the arylidene intermediate with the hydride ion. All synthesized compounds were tested for their antiradical activity against DPPH and GO free radicals. The antiradical activity of the 3-arylmethyl 4-hydroxyquinolin-2 (1H)-ones was comparable to or even higher than that of some commercially widely used antioxidants like BHT, TBHQ, or a-tocopherol. (c) 2022 Elsevier Ltd. All rights reserved.

Key words

3-Arylmethyl4-hydroxyquinolin-2(1H)-one/Knoevenagel condensation/Michael&nbsp/reaction/One-pot/Antiradical activity/Antioxidant/FREE MICROWAVE SYNTHESIS/EFFICIENT SYNTHESIS/C-ALLYLATION/GLYCINE-SITE/DERIVATIVES/SOLVENT/ALDEHYDES/KINETICS/CASCADE/QUINOLINONES

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出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN:0040-4039
参考文献量65
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