Stable Bicyclic Functionalized Nitroxides: The Synthesis of Derivatives of Aza-nortropinone-5-Methyl-3-oxo-6,8-diazabicyclo[3.2.1]-6-octene 8-oxyls
| Autor: | L. N. Grigor'eva, Konstantin A. Lomanovich, Dmitrii G. Mazhukin, Alexsei Ya. Tikhonov |
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| Rok vydání: | 2021 |
| Předmět: |
Steric effects
Acetylacetone Radical Pharmaceutical Science acetylacetone Article Analytical Chemistry Catalysis chemistry.chemical_compound QD241-441 Drug Discovery base-catalyzed recyclization Organic chemistry Physical and Theoretical Chemistry Octene 3-imidazoline nitroxide TEMPON Bicyclic molecule Organic Chemistry Nitroxyl bicyclic nitroxide 8-hydroxy-5-methyl-3-oxo-6 8-diazabicyclo[3.2.1]-6-octene condensation chemistry Chemistry (miscellaneous) Alcohol oxidation Molecular Medicine |
| Zdroj: | Molecules Molecules, Vol 26, Iss 3050, p 3050 (2021) Volume 26 Issue 10 |
| ISSN: | 1420-3049 |
| Popis: | In recent decades, bicyclic nitroxyl radicals have caught chemists’ attention as selective catalysts for the oxidation of alcohols and amines and as additives and mediators in directed C-H oxidative transformations. In this regard, the design and development of synthetic approaches to new functional bicyclic nitroxides is a relevant and important issue. It has been reported that imidazo[1,2-b]isoxazoles formed during the condensation of acetylacetone with 2-hydroxyaminooximes having a secondary hydroxyamino group are recyclized under mild basic catalyzed conditions to 8-hydroxy-5-methyl-3-oxo-6,8-diazabicyclo[3.2.1]-6-octenes. The latter, containing a sterically hindered cyclic N-hydroxy group, upon oxidation with lead dioxide in acetone, virtually quantitatively form stable nitroxyl bicyclic radicals of a new class, which are derivatives of both 2,2,6,6-tetramethyl-4-oxopiperidine-1-oxyl (TEMPON) and 3-imidazolines. |
| Databáze: | OpenAIRE |
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