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Synthese und Reaktivität von 2- und 3-hydroxylierten Dihydro-1,4-Benzoxazinen

Synthesis and reactivity of 2- and 3-hydroxylated dihydro-1,4-benzoxazines

Studien zur Synthese von 1,4-Oxazinen, 3. Mitt.

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Abstract

2 can be pyrrolized to yield3 a, which in turn may be hydrolyzed with HCl to3 b. Acetylation of3 a followed by a reaction with trifluoroacetic acid (TFA) gives3 e. Elimination of ethanol from3 a or of water from3 e is not possible. Treatment of1 a with pyridine/acetic anhydride andTFA or with acetic acid/acetic anhydride affords4 a and4 b, resp. Reaction of4 b in benzene/p-toluenesulfonic acid for 2 hours yields both ethers5I and5II, whereas after 6 hours 4-acetyl-4H-1,4-benzoxazine (6) is obtained. The structures of all products are established by chemical and spectroscopic methods.

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Literatur

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Mitteilung:H. Bartsch, W. Kropp undM. Pailer, Mh. Chem.110, 257 (1979).

Teile aus der DissertationW. Kropp, Universität Wien, 1977.

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Bartsch, H., Kropp, W. & Pailer, M. Synthese und Reaktivität von 2- und 3-hydroxylierten Dihydro-1,4-Benzoxazinen. Monatshefte für Chemie 110, 267–278 (1979). https://doi.org/10.1007/BF00911914

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Keywords

  • 4-Acetyl-4H-1,4-benzoxazine
  • 2-Hydroxydihydro-1,4-benzoxazines, reactivity of
  • 3-Hydroxydihydro-1,4-benzoxazines, reactivity of