Configuration and NMR study of tricyclic oxazines fused to a norbornene or norbornane skeleton

✍ Scribed by P. Sohár; G. Stájer; G. Bernáth

• Book ID: 102963337
• Publisher: John Wiley and Sons
• Year: 1983
• Tongue: English
• Weight: 619 KB
• Volume: 21
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/omr.1270210812

✦ Synopsis

Tricyclic oxazines fused with norbornene or norbornane were synthesized for pharmacological and stereochemical purposes. Analogous oxszin-2-0nes and -2-thiones were also obtained. The diendo or diexo anellation of the hetero ring to the norbornene or norbornane skeleton was codhued by 'H and =C spectral data. The assignment of the proton sign& was proved and the proton-proton coupling values were determined by double resonance experiments. With mono-and dichloroacetyl chloride, the oxazines fused to norbornene gave azetidinones which are mixtures of two isomers. The mixtures were separated into homogeneous substances, the configuration and conformation of which were determined via Merentid NOE experiments.