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Organophotocatalytic Functionalization of 3,4-Dihydroquinoxalin-2-ones with Isoxazol-5-amines Using Visible Light

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide An organophotocatalytic strategy for the functionalization of 3,4-dihydroquinoxalin-2-ones with isoxazol-5-amines is reported. Using commercially available organophotocatalysts under visible-light irradiation and mild reaction conditions, a series of 20 seven 3,4-dihydroquinoxalin-2(1 H )-one derivatives bearing a 5-aminoisoxazol-4-yl moiety at C-3 have been synthesized. The alkylation of 5-aminoisoxazole proceeds in a chemoselective manner, affording substitution exclusively at the C-4 position of this heterocycle. This process was also scaled up to 1 mmol, revealing the formation of an isoxazol-2-one derivative as a byproduct. The mechanism of this transformation has also been investigated through steady-state luminescence quenching experiments among other techniques.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c02592