Synthesis of 4<Emphasis Type="Italic">H</Emphasis>-imidazole-5-carbaldoxime 3-oxides and 4<Emphasis Type="Italic">H</Emphasis>-imidazole-5-carbonitrile 3-oxides |
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| Authors: | I A Kirilyuk D A Morozov Yu S Tabatchikova V S Medvedev A V Lebedev G V Romanenko T V Rybalova I A Grigor’ev |
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| Institution: | (1) N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090 Novosibirsk, Russian Federation;(2) Novosibirsk State University, 2 ul. Pirogova, 630090 Novosibirsk, Russian Federation;(3) International Tomography Center, Siberian Branch of the Russian Academy of Sciences, 3a ul. Institutskaya, 630090 Novosibirsk, Russian Federation |
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| Abstract: | The condensation of 3-hydroxyamino-3-methylbutan-2-one or 3-ethyl-3-hydroxyamino-pentan-2-one with aldehydes and ammonia afforded
a series of new 1-hydroxy-4-methyl-2,5-dihydroimidazoles, whose oxidation gave rise to the corresponding 5-methyl-4H-imidazole 3-oxides. The latter, like 1-hydroxy-4-methyl-2,5-dihydroimidazoles, react with PriONO in the presence of bases to form 4H-imidazole-5-carbaldoxime 3-oxides, which are transformed into 4H-imidazole-5-carbonitrile 3-oxides in the reaction with TsCl in the presence of Et3N. The by-products produced in different steps of the synthesis were isolated and characterized.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1487–1503, July, 2008. |
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| Keywords: | α -hydroxyamino ketones 4H-imidazole 3-oxides nitrosation nitrones 2 5-dihydroimidazoles |
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