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

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

Journal

Arkivoc
ISSN: 1424-6376

Output data

Year: 2011, Volume: 2011, Number: 8, Pages: 76-98 Pages count : 23 DOI: 10.3998/ark.5550190.0012.806

Authors

Tretyakov Evgeny V. ¹ , Utepova Irina A. ² , Varaksin Mikhail V. ² , Tolstikov Svyatoslav E. ¹ , Romanenko Galina V. ¹ , Bogomyakov Artem S. ¹ , Stass Dmitry V. ³ , Ovcharenko Victor I. ¹ , Chupakhin Oleg N. ^2,4

Affiliations

1	International Tomography Center, Siberian Branch of the Russian Academy of Sciences, 3a Institutskaya str., 630090 Novosibirsk, Russian Federation
2	Department of Organic Chemistry, Ural Federal University, 19 Mira str., Ekaterinburg, 620002, Russian Federation
3	Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, 3 Institutskaya str., 630090, Novosibirsk, Russian Federation
4	Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 S. Kovalevskoy str., Ekaterinburg, 620990, Russian Federation

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-1Himidazol-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 buten3-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) isoxazol5-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.

Tretyakov E.V. , Utepova I.A. , Varaksin M.V. , Tolstikov S.E. , Romanenko G.V. , Bogomyakov A.S. , Stass D.V. , Ovcharenko V.I. , Chupakhin O.N.
New approach to synthesis of nitronyl and imino nitroxides based on SNH methodology
Arkivoc. 2011. V.2011. N8. P.76-98. DOI: 10.3998/ark.5550190.0012.806

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