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Synthesis, stereochemistry, and isomeric transformations of cis- and trans-1,2-dimethyl-4-aryl-5-aroyl-2-imidazolines

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Abstract

The corresponding trans- and cis-1,2-dimethyl-4-aryl-5-aroyl-2-imidazolines were obtained from complexes of cis- and trans-1-methyl-2-aryl-3-aroylaziridines with BF3 by heating with acetonitrile. The reaction proceeds with inversion of the configuration of the starting 3-aroylaziridines. In the presence of bases the complexes of cis-1,2-dimethyl-4-aryl-5-aroyl-2-imidazolines readily undergo isomerization to the corresponding trans analogs. The structures of the products were established on the basis of the IR, PMR, and mass spectra and the results of elementary analysis. The configurations of the compounds were determined by means of the Overhauser nuclear effect.

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Authors and Affiliations

  1. V. I. Lenin Belorussian State University, 220080, Minsk

    I. G. Tishchenko, O. N. Bubel' & V. A. Konovalov

Authors
  1. I. G. Tishchenko
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  2. O. N. Bubel'
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  3. V. A. Konovalov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 952–957, July, 1981.

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Tishchenko, I.G., Bubel', O.N. & Konovalov, V.A. Synthesis, stereochemistry, and isomeric transformations of cis- and trans-1,2-dimethyl-4-aryl-5-aroyl-2-imidazolines. Chem Heterocycl Compd 17, 705–710 (1981). https://doi.org/10.1007/BF00506041

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  • DOI: https://doi.org/10.1007/BF00506041

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