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The preparation of 5‐phenacylisoxazoles and 5‐hydroxyphenyl‐isoxazoles and ‐pyrazoles by the condensation of C( a )‐dianions with ethyl benzoylacetate and methyl salicylate
Author(s) -
Livingston Melanie J.,
Chick Marlisa F.,
Shealy Ernest O.,
Beam Charles F.
Publication year - 1982
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.5570190141
Subject(s) - lithium diisopropylamide , chemistry , methyl salicylate , condensation , lithium (medication) , organic chemistry , aqueous solution , medicinal chemistry , aqueous medium , ion , medicine , ecology , physics , deprotonation , biology , endocrinology , thermodynamics
C(α), O ‐Dilithiooximes and C(α), N ‐Dilithiophenylhydrazones were prepared in an excess of lithium diisopropylamide (LDA). The former was condensed with ethyl benzoylacetate and methyl salicylate, and the latter condensed with methyl salicylate. The resulting precyclization intermediates were then treated with aqueous acid, which was followed by cyclodehydration to give phenacylisoxazoles and hydroxyphenyl‐isoxazoles and ‐pyrazoles.