Grignard Reagent Addition to 5-Alkylamino-4H-Imidazole 3-Oxides: Synthesis of New pH-Sensitive Spin Probes

Igor A. Kirilyuk; Tikhon G. Shevelev; Denis A. Morozov; Ekaterina L. Khromovskih; Nikita G. Skuridin; Valery V. Khramtsov; Igor A. Grigor’ev

doi:10.1055/s-2003-38694

PAPER

Grignard Reagent Addition to 5-Alkylamino-4H-Imidazole 3-Oxides: Synthesis of New pH-Sensitive Spin Probes

Igor A. Kirilyuk*^a, Tikhon G. Shevelev^a, Denis A. Morozov^b, Ekaterina L. Khromovskih^b, Nikita G. Skuridin^c, Valery V. Khramtsov^d, Igor A. Grigor’ev^a
^a N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, pr. Acad. Lavrentieva 9, Novosibirsk 630090, Russia
Fax: +7(3832)344752; e-Mail: kirilyuk@nioch.nsc.ru;
^b Novosibirsk State University, Novosibirsk 630090, Russia
^c Institute of Chemical Kinetics & Combustion, Novosibirsk 630090, Russia
^d Dorothy M. Davis Heart & Lung Research Institute, The Ohio State University, Ohio, USA

Abstract

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Abstract

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.

Key words

Grignard reactions - amines - nitriles - imidazoles - free radicals - spin probes

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Referenzen

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