Partially fluorinated heterocyclic compounds. Part I. The preparation of some tetra- and tri-fluoroquinolines, and some reactions of 5,6,7,8-tetrafluoroquinoline

Abstract

5,6,7,8-Tetrafluoroquinoline and 2- and 4-methyl-5,6,7,8-tetrafluoroquinoline have been prepared by Skraup reactions of 2,3,4,5-tetrafluoroaniline with glycerol, crotonaldehyde, and methyl vinyl ketone, respectively. Similarly, 6,7,8- and 5,6,8-trifluoroquinoline have been prepared from 2,3,4- and 2,4,5-trifluoroaniline. Sodium methoxide, potassium hydroxide, and ammonia, as nucleophilic reagents, replaced the 7-fluorine atom in 5,6,7,8-tetrafluoroquinoline. Some of the reactions of these derivatives are described.