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Keywords = allomaltol

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4 pages, 517 KiB  
Short Note
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
by Andrey N. Komogortsev, Boris V. Lichitsky and Valeriya G. Melekhina
Molbank 2022, 2022(4), M1481; https://doi.org/10.3390/M1481 - 7 Nov 2022
Viewed by 2004
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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