The preparation of intercalating isoxazoles  via  a nitrile oxide cycloaddition | Zendy

Mosher Michael D. | Zendy; Natale Nicholas R. | Zendy

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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.

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