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

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

Journal

Organic and Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2024, Volume: 22, Number: 8, Pages: 1686-1692 Pages count : 7 DOI: 10.1039/d3ob01957h

Authors

Komogortsev Andrey N. ¹ , Melekhina Valeriya ¹ , Lichitskii Boris ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Pr., 47, Moscow 119991, Russian Federation

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.

Komogortsev A.N. , Melekhina V. , Lichitskii B.
Anionic photochemical rearrangement of 3-hydroxypyran-4-ones bearing oxazol-2-one fragment
Organic and Biomolecular Chemistry. 2024. V.22. N8. P.1686-1692. DOI: 10.1039/d3ob01957h WOS Scopus OpenAlex

Web of science:	WOS:001155371400001
Scopus:	2-s2.0-85183938834
OpenAlex:	W4391016156

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