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The preparation of quinolines and related fused‐ring heterocycles from the dianions of benzoylacetone, certain cyclic ketone oximes, or certain substituted hydrazones
Author(s) -
Mack H. Michael,
Davis Everette A.,
Kadkhodayan Babak,
Taylor Richard A.,
Duncan Dean C.,
Beam Charles F.
Publication year - 1987
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.5570240645
Subject(s) - lithium diisopropylamide , chemistry , ketone , ring (chemistry) , hydrolysis , lithium (medication) , organic chemistry , medicinal chemistry , aqueous solution , ion , medicine , deprotonation , endocrinology
C (α), O ‐Dilithiooximes, C (α), N ‐dilithiobenzoylhydrazones, or C (α), N ‐dilithiocarboalkoxyhydrazones were prepared in an excess of lithium diisopropylamide (LDA) and condensed with 2‐aminobenzophenones, or isatoic anhydrides to give intermediates that were treated with aqueous acid, which caused their hydrolysis, cyclodehydration and/or linear dehydration to give products which were substituted quinolines or related fused‐ring heterocycles ( e.g. , cycloheptaquinolines). Dilithiobenzoylacetone was condensed with 2‐aminobenzophenones, which was followed by acid cyclodehydration to substituted 2‐phenacylquinolines.