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Über Reaktionen von Alkylbiguaniden mit Benzoin beimpH der Biguanidbasen

Reactions of alkylbiguanides with benzoin at thepH of the biguanide bases

  • Organische Chemie Und Biochemie
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Summary

Alkylbiguanides2 a–e react with benzoin (1) at thepH of the base in different ways.1 undergoes in presence of2 a, c oxidation to benzoic acid which reacts with the bases2 a, c to yield 4-phenyl-1,3,5-triazinamines3 c, 4 c; in presence of2 b 1 is transformed to benzil, which reacts with2 b under rearrangement to yield 1-(4-oxo-5,5-diphenyl-2-imidazolin-2-yl)-3,3-dimethylguanidine (5 b). However, the cycloalkylbiguanides2 d, e, react in presence of nitrogen as well as oxygen with1 to yield piperidine-1-[N-(4,5-diphenylimidazol-2-yl)-carboxamidine] (7 d), resp. morpholine-4-[N-(4,5-diphenylimidazol-2-yl)-carboxamidine] (7 e). The structure of7 e was established by means of an X-ray structure analysis. All proton- and carbon resonances were assigned on the basis of 2-dimensional NMR data.

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Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Karl-Franzens-Universität Graz, A-8010, Graz, Österreich

    H. W. Schramm & M. Schubert-Zsilavecz

  2. Institut für Physikalische Chemie, Karl-Franzens-Universität Graz, A-8010, Graz, Österreich

    A. I. Saracoglu & Ch. Kratky

Authors
  1. H. W. Schramm
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  2. M. Schubert-Zsilavecz
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  3. A. I. Saracoglu
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  4. Ch. Kratky
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Schramm, H.W., Schubert-Zsilavecz, M., Saracoglu, A.I. et al. Über Reaktionen von Alkylbiguaniden mit Benzoin beimpH der Biguanidbasen. Monatsh Chem 122, 1063–1073 (1991). https://doi.org/10.1007/BF00811115

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  • DOI: https://doi.org/10.1007/BF00811115

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