4a,7a-Dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[b]pyridine-4,4′-pyran]-2,7(1H,3H)-dione

4a,7a-Dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[b]pyridine-4,4′-pyran]-2,7(1H,3H)-dione Full article

Journal

Molbank
ISSN: 1422-8599

Output data

Year: 2022, Volume: 2022, Number: 4, Article number : M1481, Pages count : DOI: 10.3390/m1481

Authors

Komogortsev Andrey N. ¹ , Lichitsky Boris V. ¹ , Melekhina Valeriya G. ¹

Affiliations

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

An environment-friendly photochemical approach to the synthesis of 4a,7a-dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[b]pyridine-4,4′-pyran]-2,7(1H,3H)-dione from 2-(4-(3-hydroxy-6-methyl-4-oxo-4H-pyran-2-yl)tetrahydro-2H-pyran-4-yl)-N-(2-hydroxyethyl)acetamide was elaborated. The suggested method is based on the ESIPT-promoted contraction of 3-hydroxypyran-4-one fragment followed by intramolecular cyclization of generated in situ α-hydroxy-1,2-diketone intermediate. The distinctive feature of the presented protocol is the employment of water as a solvent for the considered photoreaction. The structure of the obtained photoproduct was confirmed by 1H, 13C-NMR, IR spectroscopy and high-resolution mass spectrometry.

Komogortsev A.N. , Lichitsky B.V. , Melekhina V.G.
4a,7a-Dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[b]pyridine-4,4′-pyran]-2,7(1H,3H)-dione
Molbank. 2022. V.2022. N4. M1481 . DOI: 10.3390/m1481 WOS Scopus OpenAlex

Web of science:	WOS:000903366700001
Scopus:	2-s2.0-85144740136
OpenAlex:	W4308475518

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