A ring-fission/C–C bond cleavage reaction with an N-alkyl-N-methyl-N-[(5-phenyl-1,2,4-oxadiazol-3-yl)methyl]amine |
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Authors: | Christine Jger Christian Laggner Kurt Mereiter Wolfgang Holzer |
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Institution: | a Institute of Pharmaceutical Chemistry, University of Vienna, Pharmaziezentrum, Althanstraße 14, A-1090, Vienna, Austria b Institute of Chemical Technology and Analytics, Technical University of Vienna, Getreidemarkt 9/164, A-1060, Vienna, Austria |
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Abstract: | The reaction of N-(3,4-dichlorophenethyl)-N-methylamine (1) with 3-chloromethyl-5-phenyl-1,2,4-oxadiazole (2) was investigated. Employment of an equimolar amount of 1 and 2 in the presence of potassium carbonate led to the expected tertiary amine 3 (N-(3,4-dichlorophenyl)ethyl]-N-methyl-N-(5-phenyl-1,2,4-oxadiazol-3-yl)methyl]amine), whereas an excess of 1 and prolonged reaction time resulted in ring fission of the oxadiazole system in 3 and finally in the formation of N′-benzoyl-N-(3,4-dichlorophenyl)ethyl]-N-methylguanidine (4) and N,N′-bis(3,4-dichlorophenyl)ethyl]-N,N′-dimethylmethanediamine (5). The structures of products 3–5 were determined by means of 1H and 13C NMR-spectroscopy, mass spectrometry and IR-spectroscopy, for 3 (as picrate) and 4 also X-ray structure analysis was employed. A possible mechanism of the reaction pathway leading to compounds 4 and 5 is proposed. |
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Keywords: | 1 2 4-oxadiazole ring opening C–C bond cleavage X-ray structure analysis |
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