2,2,2-trifluoroethanol-promoted access to symmetrically 3,3-disubstituted quinoline-2,4-diones

SELVERO, MARCEL MANKE; LEDESMA, GABRIELA N.; ABRAM, ULRICH; SCHULZ-LANG, ERNESTO; MOREL, ADEMIR FARIAS; LARGHI, ENRIQUE L.

JOURNAL OF FLUORINE CHEMISTRY

ELSEVIER SCIENCE SA

Año: 2020 vol. 234 p. 109520 - 109526

0022-1139

The unprecedented use of 2,2,2-trifluoroethanol as reaction solvent provided a facile and convenient access to symmetrically 3,3-disubstitued quinoline-2,4-diones in moderate to excellent yields and high regioselectivity, by reaction of 4-hydroxy-2-quinolones with electrophiles like methyl iodide, as well as benzyl and allyl bromides in the presence of K2CO3. Silver (I) oxide is required to increase the yield of the methylations.