Selective transformation of tricyclic peroxides with pronounced antischistosomal activity into 2-hydroxy-1,5-diketones using iron (II) salts

The present work deals with selective transformations of peroxides into organic compounds via the cleavage of the O–O bond using variable valence metals. A selective transformation of tricyclic peroxides promoted by Fe2+ salts was discovered. This selective transformation is unexpected for compounds...

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Bibliographic Details
Published in:Tetrahedron 2016-06, Vol.72 (24), p.3421-3426
Main Authors: Terent'ev, Alexander O., Pastukhova, Zhanna Yu, Yaremenko, Ivan A., Novikov, Roman A., Demchuk, Dmitry V., Bruk, Lev G., Levitsky, Dmitry O., Fleury, Fabrice, Nikishin, Gennady I.
Format: Article
Language:English
Subjects:
Antiparasitic
Bonding
Cleavage
Cycles
Diketones
Iron
Iron (II) salts
Organic compounds
Peroxides
Synthesis
Tetrahedrons
Transformations
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Summary:The present work deals with selective transformations of peroxides into organic compounds via the cleavage of the O–O bond using variable valence metals. A selective transformation of tricyclic peroxides promoted by Fe2+ salts was discovered. This selective transformation is unexpected for compounds with structural features which allow diverse decomposition pathways. 2-Hydroxy-1,5-diketones are prepared in yields up to 92% in the reactions of tricyclic peroxides with FeSO4, Fe(ClO4)2, or FeCl2. This is a new preparative method for the synthesis of 1,5-diketones. 2-Hydroxy-1,5-diketones in CDCl3 at 25 °C exist mainly in the open-chain form of the hydroxyketone over the cyclic hemiacetal. The results of this work can be of interest to understand the mechanism of the antiparasitic action of peroxides. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.04.054