<原報>Oxazoline および Oxazolidine 誘導体の合成

概要

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As shown in Chart 1,an equimolar mixture of 2-amino-2-oxazoline (1a) or 2-Alkylamino-2-oxazoline (1b, c) and Alkylisothiocyanate (2) or Alkylisocyanate (7) gave A-type compounds; 2-imino or 2-Alkylimino derivatives, (3) or (8). The 2-imino-3-(N-alkylthiocarbamoyl) oxazolidine (3a, b, c) or 2-imino-3-(N-alkylcarbamoyl) oxazolidine (8a, b) were isomerized to a higher melting compound (B-type) by heating at about 140°(oil bath temperature) in toluene containing 2,3 drops pyridine. The reaction of (1b, c) with (2) or (7) gave a product, 3-(N-Alkylthiocarbamoyl)-2-alkyliminooxazolidine (3d-h) and 3-(N-Alkylcarbamoyl)-2-alkyliminooxazolidine (8c, d) which showed no change in melting point by heating. Treatment of A-type derivatives (3) or (8) with dil. H_2SO_4 at room temperature or by heating at about 95°(boiling water bath temperature) gave 2-oxo derivatives (5) or (10) which were identified by elementary analysis, Mass and NMR. It was confirmed that 3-(N-Alkylthiocarbamoyl)-2-oxooxazolidine (5) obtained from 2-oxooxazolidine (6) and (2) by heating in pyridine at 150°through the route D was identical with the compound obtained through the route C from IR and UV data. We wish to report Mass and NMR data for these compounds.
共立薬科大学の論文