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Friedländer syntheses with o ‐aminoaryl ketones. III. Acid‐catalyzed condensations of o ‐aminobenzophenone with polyfunctional carbonyl compounds
Author(s) -
Fehnel Edward A.
Publication year - 1967
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.5570040417
Subject(s) - chemistry , moiety , ring (chemistry) , catalysis , medicinal chemistry , closure (psychology) , base (topology) , stereochemistry , organic chemistry , mathematical analysis , mathematics , economics , market economy
The acid‐catalyzed condensations of o ‐aminobenzophenone with a variety of diketones, ketoesters, ketoacids, and representatives of several other classes of polyfunctional carbonyl compounds containing the ‐COCH 2 ‐ moiety have been investigated. Under the conditions used, normal Friedländer‐type ring‐closure was found to occur in all cases, giving good yields of substituted quinolines which have been identified as the 4‐phenyl analogs of the products obtained in classical base‐catalyzed Friedländer condensations with o ‐aminobenzaldehyde. The method appears to be quite general and should provide a convenient synthetic route to a previously inaccessible series of 4‐arylquinolines.