Selective transformation of tricyclic peroxides with pronounced antischistosomal activity into 2-hydroxy-1, 5-diketones using iron (II) salts. Issue 24 (16th June 2016)

• Record Type: Journal Article
• 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.
• Is Part Of: Tetrahedron. Volume 72:Issue 24(2016)
• Page Start: 3421
• Page End: 3426
• Publication Date: 2016-06-16
• Subjects: Peroxides -- Diketones -- Cycles -- Iron (II) salts -- Antiparasitic; AEDXYXLQGVJVJP-UHFFFAOYSA-N -- IBDAMNLXQUBFPI-UHFFFAOYSA-N -- BMGJPRKMALEKPE-UHFFFAOYSA-N -- CSGVLJZINXCWGB-UHFFFAOYSA-N -- RPYXQPATQOBNGK-UHFFFAOYSA-N -- QORVGKUBIMBUJR-UHFFFAOYSA-N -- DCICOAQYEJUDCY-UHFFFAOYSA-N -- WUWOZSJWGAXIAD-UHFFFAOYSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.04.054
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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 Fe 2+ 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. Graphical abstract: