Chemistry Letters, Vol.33, No.9, 1206-1207, 2004
4-difluoromethylated quinoline synthesis via intramolecular S(N)2' reaction of alpha-trifluoromethylstyrenes bearing imine moieties
Intramolecular cyclization of o-methyleneamino-substituted alpha-trifluoromethylstyrenes is promoted by DBU and a catalytic amount of KCN to provide 4-(difluoromethyl)quinolines. The reaction proceeds via (i) the generation of carbon nucleophiles from the imine moieties, (ii) their intramolecular S(N)2' reaction with loss of a fluoride ion, and (iii) subsequent aromatization by alkene isomerization.