Transformations of conjugated enamines of the imidazolidine 1-oxide series in the Vilsmeier-Haack reaction |
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Authors: | Ch S Becker G I Roshchupkina T V Rybalova Yu V Gatilov V A Reznikov |
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Institution: | (1) Novosibirsk State University, 2 ul. Pirogova, 630090 Novosibirsk, Russian Federation;(2) 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 |
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Abstract: | In some cases, the reactions of enaminones of the imidazolidine 1-oxide series with the Vilsmeier reagent afford electrophilic
substitution products containing the dimethyl-aminomethylene group. In an acidic medium, these products undergo either hydrolytic
elimination of the dimethylaminomethylene moiety or hydrolysis of the latter to form the aldehyde group. The reaction of nitroenamine,
which is a derivative of imidazolidine 1-oxide, with the Vilsmeier reagent produces furoxane, viz., the nitroxyl biradical. Reduction of the latter affords the dioxime biradical.
Dedicated to the memory of Academician N. N. Vorozhtsov on the 100th anniversary of his birth.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1165–1170, June, 2007. |
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Keywords: | nitroxides enaminones nitroenamine Vilsmeier-Haack reaction imidazolidines |
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