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Photochemical Conversion of Isoxazoles to 5‑Hydroxyimidazolines

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journal contribution
posted on 14.04.2020, 20:08 by Taiki Morita, Shinichiro Fuse, Hiroyuki Nakamura
Photochemical conversion of isoxazole I to 5-hydroxyimidazoline VII proceeded via the trapping of the photogenerated acylazirine III with amines under UV light irradiation. This is the first report of the efficient synthesis of 5-hydroxyimidazolines that are not readily accessible by other means. 5-Hydroxyimidazolines were also converted into multisubstituted imidazoles in one step by treatment with trifluoroacetic anhydride (TFAA) and 2,6-lutidine in dichloromethane.