Facile and Convenient Syntheses for Fluorine-Containing Pyrazolo[4,3-c]quinolines, Isoxazoloquinolines, and 1,4-Diazepino[6,5-c]quinolines

Synthesis of 5-(Fluoroalkyl)isoxazole Building Blocks by Regioselective Reactions of Functionalized Halogenoximes

“…It is not surprising therefore that synthesis of fluoroalkyl-substituted isoxazoles have attracted significant interest. A classical approach to the synthesis of these compounds relies on the heterocyclization reaction of fluorinated 1,3-bis-electrophiles and hydroxylamine (Scheme , A). − A similar method involves condensation of enolizable oximes with trifluoroacetates (Scheme , B) . In addition to that, deoxofluorination of the oxygen-containing isoxazoles, for example, alcohols or aldehydes, was described (Scheme , C). , An alternative approach includes [3 + 2] cycloaddition − of fluoroalkyl-substituted alkenes, − alkynes, − or enolizable ketones − and generated in situ nitrile oxides (Scheme , D).…”

Computational Study for the Aromatic Nucleophilic Substitution of 4-Dimethylamino-3-trifluoroacetyl- quinoline with Various Nucleophiles

“…A number of researchers have engaged in exploring synthetic methodologies for novel kinds of fluorine-containing heterocycles because of their attractive character which often demonstrates high and unique biological activity in the field of life science research. [1][2][3][4] In recent years, we have succeeded in establishing the convenient synthetic methods which enable us to access novel fluorine-containing dibenzo[b,h] [1,6]naphthyridines, thiochromeno [3,2-c]quinolines, and chromeno [3,2-c]quinolines via 4-dimethylamino-3-trifluoroacetylquinoline 1 as a synthetic intermediate. 5 We also reported novel synthesis of 1H-and 2H-pyrazolo [4,3-c]quinolines, 6 isoxazoloquinolines, 6 4-diazepino [6,5-c]quinolines, 6 pyrimido [5,4-c]quinolines, 7 and benzo[h] [1,6]naphthyridines 7 using the reaction of 1 with bifunctional nucleophiles.…”