Signs of formation and chemical evolution of zwitterions in the reaction of 1-methyl-imidazole with cyanophenylacetylene and benzaldehyde

Primary monitoring of the three-component reaction of 1-methylimidazole with cyanophenylacetylene and benzaldehyde by EPR, UV, NMR, and IR spectroscopy has been carried out. Experimental evidence has been obtained for the formation of zwitterions and carbenes of the imidazole series as intermediates...

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Veröffentlicht in:	Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2012, Vol.47 (11), p.1390
Hauptverfasser:	Andriyankova, L.V, Belyaeva, K.V, Nikitina, L.P, Mal'kina, A.G, Vakul'skaya, T.I, Khutsishvili, S.S, Sinegovskaya, L.M, Trofimov, B.A
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes Chemical properties Nitrogen Nuclear magnetic resonance spectroscopy
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Zusammenfassung:	Primary monitoring of the three-component reaction of 1-methylimidazole with cyanophenylacetylene and benzaldehyde by EPR, UV, NMR, and IR spectroscopy has been carried out. Experimental evidence has been obtained for the formation of zwitterions and carbenes of the imidazole series as intermediates of a new functionalization reaction of the imidazole ring leading to 2-benzoyl-3-(1-methyl-1H-imidazol2-yl)-3- phenylpropanenitrile. Keywords: aldehydes, carbenes, cyanoacetylenes, 1-substituted imidazoles, zwitterions, monitoring reaction, multicomponent reactions, nucleophilic addition.
ISSN:	0009-3122
DOI:	10.1007/s10593-012-0926-1