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The preparation of intercalating isoxazoles via a nitrile oxide cycloaddition
Author(s) -
Mosher Michael D.,
Natale Nicholas R.
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320314
Subject(s) - chemistry , aldehyde , nitrile , yield (engineering) , enamine , oxime , cycloaddition , pyridinium , organic chemistry , pyridinium chlorochromate , oxide , medicinal chemistry , catalysis , materials science , metallurgy
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.