Beilstein J. Org. Chem.2024,20, 2378–2391, doi:10.3762/bjoc.20.202
: antioxidant activity; catecholthioethers; heterocycles; redox-transformations; thiones; Introduction
Synthetic derivatives of polyphenols, in particular catechol (hydroquinone), represent a promising group of pharmacologically active substances [1][2]. Catechol-containing compounds demonstrate
derivatives are used as ligands in the synthesis of metal complexes (Ni(II), Pd(II), Pt(II), Cu(I), Ag(I) etc.) exhibiting antibacterial and antitumor activity [34].
In most cases, polyfunctional catecholthioethers were obtained by Michael reaction via the interaction of o-, p-benzoquinone and the
/prooxidant, and antiradical activity was carried out for the catechols synthesized in this work.
Results and Discussion
Synthesis
The interaction of 3,5-di-tert-butyl-o-benzoquinone with the corresponding thiols in ethanol at room temperature under argon leads to the formation of catecholthioethers 1–3 (69
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Graphical Abstract
Scheme 1:
Synthesis of catechol-containing compounds 1–9.