Synthesis · 1997 · 26 citations · 0 references
PharmacyMedicinal ChemistryPharmacologyDrug DiscoverySynthetic Medicinal ChemistryCholinergic NeurochemistryCholinergic PharmacologyEster-to-amide ConversionIsoxazole ChemistryIsoxazole SynthesisMedicinal Chemistry Applications
A concise, regiocontrolled route to isoxazoles, based on the condensation of an ester with a metallated imine, has been developed. The intermediate vinylogous amides react smoothly with hydroxylamine to provide, after dehydration, substituted isoxazoles. The method has been used for the multi-kilo scale preparation of ABT-418, a novel cholinergic channel activator.