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 |
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Authors: | Matthias Scheunemann Dietlind Sorger Osama Sabri Barbara Wenzel |
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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 |
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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. |
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Keywords: | Diepoxide Ring-opening Hexahydro-benzo[1,4]oxazin-3-ones VAChT |
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