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Synthese von 5-Dialkylamino-1,2-oxazolen aus N,N-Dialkyl-β-amino-α,β,γ,δ-ungesättigten Thioamiden

Syntheses of 5-dialkylamino-1,2-oxazoles from N,N-dialkyl-β-amino-α,β,γ,δ-unsaturated thioamides

  • Organische Chemie Und Biochemie
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Summary

3-Amino-2,4-pentadienthioamides, which were obtained from 6-dialkylamino-2H-thiopyrane-4(3H)iminium halides by alkali hydrolysis, react with hydroxylamine hydrochloride in a [C-C-C] + [N-O]-addition to give selectively 5-amino-3-alkenyl-1,2-oxazoles. These oxazoles have been identified by13C and1H NMR spectroscopic analysis. The configuration of these compounds was established on the basis of the coupling constants and 2D-NOESY-experiments. The position of the substituents has been determined by analysis of the fragmentation pattern.

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Authors and Affiliations

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

    H. Auer, R. Weis, K. Schweiger & M. Schubert-Szilavecz

Authors
  1. H. Auer
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  2. R. Weis
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  3. K. Schweiger
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  4. M. Schubert-Szilavecz
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Herrn Prof. Dr. Robert Ott zum 70. Geburtstag gewidmet

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Auer, H., Weis, R., Schweiger, K. et al. Synthese von 5-Dialkylamino-1,2-oxazolen aus N,N-Dialkyl-β-amino-α,β,γ,δ-ungesättigten Thioamiden. Monatsh Chem 125, 571–577 (1994). https://doi.org/10.1007/BF00811850

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  • DOI: https://doi.org/10.1007/BF00811850

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