Nonyl Acridine Orange as a Prospective Photocatalyst in Chalcogenylation of Coumarins and Quinolinones

• DOI: 10.1021/acs.joc.2c01803
• Publication Date: 2022-10-31T04:40:17Z
• Authors: Sindija Lapcinska; Pavels Dimitrijevs; Pavel Arsenyan
• Keywords: Acridine orange; Acridine

A mild and efficient method for preparation of 3-sulfenyl 3-selenyl coumarins quinolinones mediated by artificial light or sunlight is presented. The elaborated protocol highlights the use nonyl acridine orange as a photocatalyst to generate sulfenyl radical from thiols that further trapped heterocycle. utility justified diverse scope thiols, including short cysteine-containing peptides. same reaction conditions can be applied quinolinones. Various protected unprotected selenocysteine-containing peptides were successfully utilized demonstrating high tolerance amino acids with sensitive groups (Arg, Lys, Trp, His, Tyr).