Über Reaktionen von Alkylbiguaniden mit Benzoin beimpH der Biguanidbasen |
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| Authors: | H W Schramm M Schubert-Zsilavecz A I Saracoglu Ch Kratky |
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| Institution: | (1) Institut für Pharmazeutische Chemie, Karl-Franzens-Universität Graz, A-8010 Graz, Österreich;(2) Institut für Physikalische Chemie, Karl-Franzens-Universität Graz, A-8010 Graz, Österreich |
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| Abstract: | 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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| Keywords: | Benzoin reaction with alkylbiguanides Imidazoles {piperidine-1- resp morpholine-4-[N-(4 5-diphenylimidazol-2-yl)-carboxamidine] 1-(4-oxo-5 5-diphenyl-2-imidazolin-2-yl)-3 3-dimethylguanidine} Triazines [N-(4-amino-6-phenyl-1 3 5-triazin-2-yl)-benzamide] NMR X-ray analysis |
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