Abstract: 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.

Cite: Grigor'eva L.N. , Tikhonov A.Y. , Lomanovich K.A. , Mazhukin D.G.
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
Molecules. 2021. V.26. N10. 3050 . DOI: 10.3390/molecules26103050 WOS Scopus РИНЦ

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May 20, 2021

Identifiers:

Web of science	WOS:000655205800001
Scopus	2-s2.0-85107291104
Elibrary	46862884
OpenAlex	W3165691502

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