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

Author： Balaneva N.   Radchenko O.   Glazunov V.   Novikov V.  

Publisher： Springer Publishing Company

ISSN： 1066-5285

Source： Russian Chemical Bulletin, Vol.61, Iss.10, 2012-10, pp. : 1900-1908

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Abstract

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.

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