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Synthesis and properties of fluorine‐containing heterocyclic compounds. I. trifluoromethyl quinolines
Author(s) -
Dey Adrienne Steinacker,
Joullié Madeleine M.
Publication year - 1965
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.5570020201
Subject(s) - chemistry , trifluoromethyl , yield (engineering) , hydrogenolysis , hydrazine (antidepressant) , raney nickel , organic chemistry , condensation , medicinal chemistry , catalysis , chromatography , alkyl , materials science , physics , metallurgy , thermodynamics
The condensation of ethyl trifluoroacetoacetate with various aromatic amines, in polyphosphoric acid at 150°, gave substituted 2‐trifluoromethyl‐4‐quinolinols. The structure of these compounds was established from a study of their infrared and ultraviolet spectra and, in some cases, by independent synthesis and cyclization of the intermediate 3‐arylaminocrotonates. The 2‐trifluoromethyl‐4‐quinolinols were converted to 2‐trifluoromethyl‐4‐chloroquinolines which were subjected to hydrogenolysis with Raney nickel to yield 2‐trifluoromethylquinolines and to treatment with an excess of hydrazine to give the corresponding hydrazino derivatives. The diazotization of 2 ‐ trifluoromethyl ‐4‐hydrazinoquinolines yielded azides which were unusually stable. The infrared and ultraviolet spectra of some of the compounds prepared are discussed.