Anionic photochemical rearrangement of 3-hydroxypyran-4-ones bearing oxazol-2-one fragment.

Autor:	Komogortsev AN; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Pr., 47, Moscow 119991, Russian Federation. dna5@mail.ru., Melekhina VG; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Pr., 47, Moscow 119991, Russian Federation. dna5@mail.ru., Lichitskii BV; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Pr., 47, Moscow 119991, Russian Federation. dna5@mail.ru.
Jazyk:	angličtina
Zdroj:	Organic & biomolecular chemistry [Org Biomol Chem] 2024 Feb 21; Vol. 22 (8), pp. 1686-1692. Date of Electronic Publication: 2024 Feb 21.
DOI:	10.1039/d3ob01957h
Abstrakt:	The photochemical behavior of in situ generated anions of 3-hydroxypyran-4-ones containing an oxazol-2-one moiety was studied. For the first time, it was demonstrated that blue LED light irradiation (450 nm) of substituted 3-hydroxypyran-4-ones in the presence of a base leads regiospecifically to the formation of isomeric 3-hydroxypyran-2-ones. Transformation of the starting 3-hydroxypyran-4-ones into the corresponding anions is necessary for the presented photoprocess. Based on the considered visible light induced rearrangement, a general method for the synthesis of 3-hydroxypyran-2-ones with an oxazol-2-one moiety was elaborated. The structure of one of the synthesized compounds was confirmed by X-ray diffraction.
Databáze:	MEDLINE
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