Grignard reagent addition to 5-alkylamino-4H-imidazole 3-oxides: Synthesis of new pH-sensitive spin probes

Grignard reagent addition to 5-alkylamino-4H-imidazole 3-oxides: Synthesis of new pH-sensitive spin probes Full article

Journal

Synthesis
ISSN: 0039-7881

Output data

Year: 2003, Number: 6, Pages: 871-878 Pages count : 8

Tags

Amines; Free radicals; Grignard reactions; Imidazoles; Nitriles; Spin probes

Authors

Kirilyuk I.A. ¹ , Shevelev T.G. ¹ , Morozov D.A. ² , Khromovskih E.L. ² , Skuridin N.G. ³ , Khramtsov V.V. ⁴ , Grigor'ev I.A. ¹

Affiliations

1	(Scopus) N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, pr. Acad. Lavrentieva 9, Novosibirsk 630090, Russian Federation
2	(Scopus) Novosibirsk State University, Novosibirsk 630090, Russian Federation
3	(Scopus) Institute of Chemical Kinetics and Combustion, Novosibirsk 630090, Russian Federation
4	(Scopus) Dorothy M. Davis Heart and Lung Research Institute, The Ohio State University, Ohio, United States

4,4-Dimethyl-4H-imidazole-5-carbaldehyde oxime 3-oxides 4 were prepared by oxidation and nitrosation of 4,5,5-trimethyl-2,5-dihydro-1H-imidazol-1-ols. The oximes 4 were converted to 5-cyano derivatives; the latter react with primary or secondary amines to form 5-(di)alkylamino-4H-imidazole 3-oxides 6. Treatment of 6 with AlkMgX and subsequent oxidation yielded stable nitroxides 4-(di)alkylamino-2,5-dihydroimidazole-1-oxyls 7, the pH-sensitive spin probes.

Kirilyuk I.A. , Shevelev T.G. , Morozov D.A. , Khromovskih E.L. , Skuridin N.G. , Khramtsov V.V. , Grigor'ev I.A.
Grignard reagent addition to 5-alkylamino-4H-imidazole 3-oxides: Synthesis of new pH-sensitive spin probes
Synthesis. 2003. N6. P.871-878. WOS Scopus РИНЦ

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