Synthesis and NMR study of norbornane/norbornene-fused tetracyclic azetidinones

P. Sohár, G. Stájer, I. Pelczer, A. E. Szabó, J. Szúnyog, G. Bernáth

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Abstract

Tetracyclic azetidinones8,9 and 12-17 were synthesized. In the cases of8 and9, the main component was isolated from the two-component product of the cycloaddition. The minor component was concentrated to give a mixture, from which a computer technique utilizing the known spectrum of the main component gave the proton resonance spectrum also of the minor component. Only one diastereomer could be isolated for the each of the analogues12-17. Reaction of the 1,3-oxazine 3 with chloroacetyl chloride gave, besides the azetidinone 12, the 1,3-oxazine [2,3-b]-1,3-oxazin-4-one derivative18. Configurations and conformations were determined by IR, 1H and 13C NMR spectroscopy.

Original languageEnglish
Pages (from-to)1721-1732
Number of pages12
JournalTetrahedron
Volume41
Issue number9
DOIs
Publication statusPublished - 1985

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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