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Sequential ring-opening of trans-1,4-cyclohexadiene dioxide for an expedient modular approach to 6,7-disubstituted (±)-hexahydro-benzo[1,4]oxazin-3-ones
Authors:Matthias Scheunemann  Dietlind Sorger  Osama Sabri  Barbara Wenzel
Affiliation:a Institute of Interdisciplinary Isotope Research, Permoserstraße 15, 04318 Leipzig, Germany
b Department of Nuclear Medicine, University of Leipzig, Stephanstraße 11, 04103 Leipzig, Germany
c Paul Flechsig Institute for Brain Research, University of Leipzig, Jahnallee 59, 04109 Leipzig, Germany
Abstract:A modular approach to novel 6-amino-7-hydroxysubstituted hexahydro-benzo[1,4]oxazin-3-ones has been developed. The method involves a sequential ring-opening of trans-1,4-cyclohexadiene dioxide with amino nucleophiles. The resultant mono-epoxide from benzylamine was converted to a general electrophilic precursor, which enables the parallel treatment with amino nucleophiles to obtain a series of cyclohexane-fused morpholin-3-ones.
Keywords:Diepoxide   Ring-opening   Hexahydro-benzo[1,4]oxazin-3-ones   VAChT
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