Cascade Assembly of Bridged N-Substituted Azaozonides: The Counterintuitive Role of Nitrogen Source Nucleophilicity
Ivan A. Yaremenko, Yulia Yu. Belyakova, Peter S. Radulov, Роман А. Новиков, Michael G. Medvedev, Nikolai V. Krivoshchapov, Igor V. Alabugin, Alexander O. Terent’ev
Abstract
Counterintuitively, the low basicity of the NH2 group in hydrazides makes them preferred nucleophiles for the synthesis of the N-substituted azaozonides in acid-catalyzed three-component condensation with 1,5-diketones and H2O2. In the case of more basic N sources, e.g., hydrazine and primary amines, such condensation does not occur under these reaction conditions. The method can be applied to a wide range of hydrazides and affords the target bicyclic azaozonides in 27–86% yields.
Topics & Concepts
ChemistryNucleophileHydrazine (antidepressant)CounterintuitiveCondensationNitrogenCascadeComponent (thermodynamics)Combinatorial chemistryCatalysisHydroxylamineOrganic chemistryPhysicsChromatographyThermodynamicsPhilosophyEpistemologySynthesis and Catalytic ReactionsChemical Synthesis and AnalysisSynthesis and Biological Evaluation