A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

Beilstein J Org Chem. 2024 Jul 31:20:1831-1838. doi: 10.3762/bjoc.20.161. eCollection 2024.

Abstract

Functionalized 5-aryldeazaalloxazines have been successfully synthesised through a one-pot, three-component reaction involving N,N-dimethylbarbituric acid, an aromatic aldehyde and aniline. By utilizing readily available reagents, this approach opens up the opportunity for the efficient formation of a variety of 5-aryldeazaalloxazines bearing electron-donating or halogen groups. This practical method is characterised by atom economy and offers a direct route to the introduction of an aryl moiety into the C(5)-position of deazaalloxazines, thereby generating novel catalysts for photoredox catalysis without the need for subsequent purification. Thus, it significantly improves existing approaches.

Keywords: catalysis; deazaalloxazine; flavin; multicomponent approach; one-pot reaction.

Grants and funding

This work was supported by the Czech Science Foundation (Grant No 21-14200K) and by the research grant CEUSUNISONO 2020/02/Y/ST4/00042, from The National Science Centre of Poland (NCN). I. W. thanks for support from Specific university research (reg. No. A2_FCHT_2023_025).