Sm-Catalyzed Synthesis and Biological Activity of Acyclic and Cyclic Azadiperoxides

Abstract

Acyclic diaminodiperoxides and cyclic azadiperoxides are synthesized by the reaction of 1,1-bis-(hydroperoxy)cycloalkanes with formaldehyde and primary arylamines in the presence of Sm-containing catalysts [SmCl₃·6H₂O, Sm(NO₃)₃·6H₂O, SmCl₃/γ-Al₂O₃, and Sm(NO₃)₃/γ-Al₂O₃]. The chemoselectivity of this three-component reaction depends on the position of the substituent (F,Cl) in the phenyl ring of the primary arylamines. Signals of the cyclic aminoperoxides were assigned considering the conformation dynamics of the tetraoxazocane cycle with two rigid peroxide bonds. The structure of the acyclic diaminodiperoxides was reliably determined by X-ray diffraction analysis. The synthesized acyclic diaminodiperoxides were found to exhibit anticancer activity.