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

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• 作者：Alexander O. Terent'ev^a ; ^{terentev@ioc.ac.ru" class="auth_mail" title="E-mail the corresponding author} ; Zhanna Yu. Pastukhova^a ; ^b ; Ivan A. Yaremenko^a ; Roman A. Novikov^a ; Dmitry V. Demchuk^a ; Lev G. Bruk^a ; ^b ; Dmitry O. Levitsky^c ; Fabrice Fleury^c ; Gennady I. Nikishin^a
• 关键词：Peroxides ; Diketones ; Cycles ; Iron (II) salts ; Antiparasitic
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：16 June 2016
• 年：2016
• 卷：72
• 期：24
• 页码：3421-3426
• 全文大小：819 K

文摘

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.