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-imidazol-2-yl)-3-phenylpropanenitrile.
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The work was carried out with the financial support of the Russian Foundation for Fundamental Investigations (grant No. 11-03-00203a), the Grants Council of the President of the Russian Federation (NSh 3230.2010.3), the Presidium of the Russian Academy of Sciences (Program 25), and the Division of Chemistry and Materials Sciences of the Russian Academy of Sciences (No. 5.1).
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Dedicated to Academician M. G. Voronkov on his 90th birthday.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1675–1679, November, 2011.
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Andriyankova, L.V., Belyaeva, K.V., Nikitina, L.P. et al. Signs of formation and chemical evolution of zwitterions in the reaction of 1-methylimidazole with cyanophenylacetylene and benzaldehyde. Chem Heterocycl Comp 47, 1390–1394 (2012). https://doi.org/10.1007/s10593-012-0926-1
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DOI: https://doi.org/10.1007/s10593-012-0926-1