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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 Научная публикация

Журнал Molecules
, E-ISSN: 1420-3049
Вых. Данные Год: 2021, Том: 26, Номер: 10, Номер статьи : 3050, Страниц : DOI: 10.3390/molecules26103050
Ключевые слова bicyclic nitroxide; condensation; acetylacetone; base-catalyzed recyclization; 3-imidazoline nitroxide; TEMPON; 8-hydroxy-5-methyl-3-oxo-6,8-diazabicyclo[3.2.1]-6-octene
Авторы Grigor'eva Larisa N. 1 , Tikhonov Alexsei Ya. 1 , Lomanovich Konstantin A. 1 , Mazhukin Dmitrii G. 1
Организации
1 (Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem SB RAS, Academician Lavrentiev Ave 9, Novosibirsk 630090, Russia

Реферат: 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.
Библиографическая ссылка: 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 OpenAlex
Файлы: Полный текст от издателя
Даты:
Опубликована online: 20 мая 2021 г.
Идентификаторы БД:
Web of science: WOS:000655205800001
Scopus: 2-s2.0-85107291104
РИНЦ: 46862884
OpenAlex: W3165691502
Цитирование в БД:
БД Цитирований
Web of science 1
РИНЦ 1
OpenAlex 1
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