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Synthesis 2003(6): 0871-0878
DOI: 10.1055/s-2003-38694
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Igor A. Kirilyuk*a, Tikhon G. Sheveleva, Denis A. Morozovb, Ekaterina L. Khromovskihb, Nikita G. Skuridinc, Valery V. Khramtsovd, Igor A. Grigor’eva
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
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Publication History

Received 6 February 2003
Publication Date:
16 April 2003 (online)

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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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