A Green and Effective Route Leading to Antiradical Agents with 3-Arylmethyl 4-Hydroxyquinolin-2(1H)-One Moiety

Tetrahedron Letters 2022
Inese Mieriņa, Agnese Stikute, Māra Jure

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 α-tocopherol.

Keywords
3-Arylmethyl 4-hydroxyquinolin-2(1H)-one | Antioxidant | Antiradical activity | Knoevenagel condensation – Michael reaction | One-pot
DOI
10.1016/j.tetlet.2022.153847
Hyperlink
https://www.sciencedirect.com/science/article/pii/S0040403922002660?via%3Dihub

Mieriņa, I., Stikute, A., Jure, M. A Green and Effective Route Leading to Antiradical Agents with 3-Arylmethyl 4-Hydroxyquinolin-2(1H)-One Moiety. Tetrahedron Letters, 2022, Vol. 99, Article number 153847. ISSN 0040-4039. Available from: doi:10.1016/j.tetlet.2022.153847

Publication language
English (en)