New approach to synthesis of nitronyl and imino nitroxides based on SNH methodology

Тип публикации: статья из журнала

Год издания: 2011

Ключевые слова: ESR spectra, Imino nitroxides, Nitronyl nitroxides, X-ray diffraction study

Аннотация: It is shown that SNH approach opens new possibilities in the synthesis of polyfunctional nitronyl and imino nitroxides. It is found that the interaction of 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1- oxyl lithium salt Li1 with 3,6-diaryl-1,2,4-triazines leads to formation of the corresponding triazines bearing nitronyl nitroxide or imino nitroxide substituent at position 5 of the heterocycle. The reaction of Li1 with pyridazine-N-oxide gives rise to nitroxide with buten-3-ynyl substituent 5. Spin-labeled 5 could be readily transformed by the use of 1,3-dipolar and nucleophilic addition reactions, as well as oxidative coupling, that gives a large group of new paramagnets: 2-(1H-pyrazol-5-yl)vinyl-, 2-ethynylcyclopropyl- , 2-(3-(ethoxycarbonyl) isoxazol-5-yl)vinyl-, 1-(pyrrolidin-1-yl)but-3-ynyl- substituted nitronyl nitroxide and a diradical - 2,2?-((1E,7E)-octa-1,7- dien-3,5-diyne-1,8-diyl)bis(4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide- 1-oxyl). The new nitroxides were characterized by X-ray single crystal data, ESR and static magnetic susceptibility measurements. © ARKAT USA, Inc.

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Издание

Журнал: Arkivoc

Выпуск журнала: Vol. 2011, Is. 8

Номера страниц: 76-98

ISSN журнала: 15517012

Авторы

  • Tretyakov E.V. (International Tomography Center, Siberian Branch of the Russian Academy of Sciences, 3a Institutskaya str., 630090 Novosibirsk, Russian Federation)
  • Utepova I.A. (Department of Organic Chemistry, Ural Federal University, 19 Mira str., Ekaterinburg, 620002, Russian Federation)
  • Varaksin M.V. (Department of Organic Chemistry, Ural Federal University, 19 Mira str., Ekaterinburg, 620002, Russian Federation)
  • Tolstikov S.E. (International Tomography Center, Siberian Branch of the Russian Academy of Sciences, 3a Institutskaya str., 630090 Novosibirsk, Russian Federation)
  • Romanenko G.V. (International Tomography Center, Siberian Branch of the Russian Academy of Sciences, 3a Institutskaya str., 630090 Novosibirsk, Russian Federation)
  • Bogomyakov A.S. (International Tomography Center, Siberian Branch of the Russian Academy of Sciences, 3a Institutskaya str., 630090 Novosibirsk, Russian Federation)
  • Stass D.V. (Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, 3 Institutskaya str., 630090, Novosibirsk, Russian Federation)
  • Ovcharenko V.I. (International Tomography Center, Siberian Branch of the Russian Academy of Sciences, 3a Institutskaya str., 630090 Novosibirsk, Russian Federation)
  • Chupakhinb O.N. (Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 S. Kovalevskoy str., Ekaterinburg, 620990, Russian Federation)

Вхождение в базы данных

  • Scopus (цитирований 10)

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