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Preparation of the 7-oxo-4-oxa-1-azabicyclo[3.2.0]hept-2-ene system and the reversible cleavage of its oxazoline ring
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1978
Year
Organic ChemistryChemistryHeterocycle ChemistryChemical DerivativePharmaceutical ChemistryOxazoline RingMedicinal ChemistryBiochemistryReversible CleavagePharmacologyNatural Product SynthesisTriethylamine LeadsBiomolecular EngineeringHeterocyclicNatural SciencesMedicineNovel ZwitterionsDerivative (Chemistry)Drug Discovery
Treatment of the derivative (5) of clavulanic acid with triethylamine leads to the endocyclic double bond isomer (6) and thence to the salt (10) which is a powerful inhibitor of β-lactamases; cleavage of the oxazoline ring of (6) with triethylamine or with pyridine gives the novel zwitterions (7) and (9) which are readily recyclised to (6) by thermolysis.