New approach to synthesis of nitronyl and imino nitroxides based on S-N(H) methodology / Tretyakov Evgeny V.,Utepova Irina A.,Varaksin Mikhail V.,Tolstikov Svyatoslav E.,Romanenko Galina V.,Bogomyakov Artem S.,Stass Dmitry V.,Ovcharenko Victor I.,Chupakhin Oleg N. // ARKIVOC. - 2011. - V. , l. 8. - P. 76-98.

ISSN/EISSN:

1551-7004 / 1551-7012

Type:

Article

Abstract:

It is shown that S-N(H) 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.

Author keywords:

Nitronyl nitroxides; imino nitroxides; S-N(H) reactions; X-ray diffraction study; ESR spectra CHEMICAL-PROPERTIES; FREE RADICALS; N-OXIDES; COMPLEXES; CHEMISTRY; ESR

DOI:

нет данных

Web of Science ID:

ISI:000293127700006

Соавторы в МНС:

Другие поля

Поле	Значение
Publisher	ARKAT USA INC
Address	C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA
Language	English
EISSN	1551-7012
Keywords-Plus	CHEMICAL-PROPERTIES; FREE RADICALS; N-OXIDES; COMPLEXES; CHEMISTRY; ESR
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	tev@tomo.nsc.ru
ResearcherID-Numbers	Tolstikov, Svyatoslav/E-1706-2012 Tretyakov, Evgeny/A-7163-2014
ORCID-Numbers	Tolstikov, Svyatoslav/0000-0001-7415-1483 Tretyakov, Evgeny/0000-0003-1540-7033 Romanenko, Galina/0000-0001-8852-2759 Bogomyakov, Artem/0000-0002-6918-5459 Stass, Dmitri/0000-0003-3510-5219
Funding-Acknowledgement	Russian Foundation for Basic Research {[}09-03-00091, 09-0312108, 08-03-00025, 10-03-00756-a]; U.S. Civilian Research and Development Foundation {[}REC-005]; Ministry of Science and Education {[}NSh-65261.2010.3]; Ural and Siberian Branches of the Russian Academy of Sciences
Funding-Text	The financial support by Russian Foundation for Basic Research (grants 09-03-00091, 09-0312108, 08-03-00025, 10-03-00756-a), U.S. Civilian Research and Development Foundation (REC-005), the Ministry of Science and Education (Grant for Leading Scientific Schools, Project NSh-65261.2010.3), Ural and Siberian Branches of the Russian Academy of Sciences is gratefully acknowledged.
Number-of-Cited-References	36
Usage-Count-Since-2013	20
Journal-ISO	Arkivoc
Doc-Delivery-Number	797KX