1,4-Conjugate addition of 2-hydroxynaphthazarins to acyclic and cyclic α,β-unsaturated ketones. Prototropic ring-chain tautomerism of the adducts

Autor:	V. P. Glazunov, N. N. Balaneva, V. L. Novikov, Oleg S. Radchenko
Rok vydání:	2012
Předmět:	chemistry.chemical_compound Stereochemistry Chemistry Cyclohexenone Methyl vinyl ketone Michael reaction Infrared spectroscopy General Chemistry Carbon-13 NMR Ring (chemistry) Tautomer Adduct
Zdroj:	Russian Chemical Bulletin. 61:1900-1908
ISSN:	1573-9171 1066-5285
Popis:	TsOH-Catalyzed reactions of 6,7-disubstituted 2-hydroxynaphthazarins and acyclic or cyclic α,β-enones afforded the corresponding Michael-type adducts, viz., 3-substituted naphthazarins in 17–78% yields. 1H and 13C NMR and IR spectroscopy showed that the adducts with cyclohexenone and methyl vinyl ketone exist in CDCl3 solutions as mixtures of open-chain and cyclic tautomers, whereas the adducts with cyclopentenones exist only as the open-chain forms.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6259df1a94022d435984cdd61db743f6 https://doi.org/10.1007/s11172-012-0264-6 Zobrazit plný text záznamu Full text from SpringerLink