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Synthesis 1989; 1989(1): 12-15
DOI: 10.1055/s-1989-27131
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5-(2-Aminoethyl)-3-aryl-5-phenylaminoisoxazole durch Ringtransformation von 2-Phenacylidenimidazolidinen

Gerd Dannhardt* , Stefan Laufer
  • *Institut für Pharmazie der Universität Regensburg, Universitätsstraße 31 D-8400 Regensburg, Federal Republic of Germany
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Publikationsdatum:
27. September 2002 (online)

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Ring Transformation of 2-Phenacylideneimidazolidines into 5-(2-Amino-ethyl)aminoisoxazoles The reaction of lithiated 2-alkyl-1-phenyl-4,5-dihydroimidazoles with benzoic esters (and pyridine analogs) leads to acylketene N,N-acetals having the structure of 2-phenacylideneimidazolidines. The E configuration of these compounds with an exocyclic double bond was substantiated by NOE experiments. With hydroxylamine hydrochloride these "endiaminones" undergo ring transformation to give 5-(2-aminoethylamino) isoxazoles which were characterized by spectrometric methods.

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