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Synthesis of 5‐methyl‐4‐oxo‐quinolinecarboxylic acids
Author(s) -
Hagen Susan E.,
Domagala John M.
Publication year - 1990
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.5570270616
Subject(s) - chemistry , moiety , trimethylsilyl , oxazoline , fluorine , molecule , chlorine , medicinal chemistry , organic chemistry , stereochemistry , catalysis
A series of 5‐methyl‐4‐oxo‐3‐quinolinecarboxylic acids was prepared in which the eight‐position was substituted with fluorine, chlorine, methyl, or hydrogen. These quinolones were synthesized from the appropriate 2‐methyl‐3,4,6‐trifluorobenzoic acids which were derived from oxazolines 8 and 16 . The oxazoline moiety served as both an ortho ‐director (where feasible) and a protecting group; a trimethylsilyl moiety was used to block the most acidic site in the molecule.