The preparation of intercalating isoxazoles via a nitrile oxide cycloaddition

Article abstract of DOI:10.1002/jhet.5570320314

Pyridinium chlorochromate oxidation of 9-methylacridine (2) affords the corresponding aldehyde 3 in good yield. Conversion of the aldehyde to the hydroximinoyl chloride 5a was accomplished via reaction of the corresponding oxime with N-chlorosuccinimide. Dipolar addition to the enamine of ethylacetoacetate provided the corresponding isoxazoles 1 in good yield.