Synthesis of new trifluoromethyl-containing cycloalka[b]quinolines derived from alkoxycycloalkenes

Abstract

The synthesis of a series of trifluoromethyl-cycloalka[b]quinolines (5a, 6a, 6c-e) in 15-30% yields, by intramolecular cyclization reactions of the readily available intermediates 2-trifluoroacetyl-1-(arylamino)-cycloalkenes (3a-f and 4a-f) using poly-phosphoric acid (PPA) is reported. Compounds 3 and 4 are obtained from the reaction of 2-trifluoroacetyl-1-methoxycycloalkenes 1 (n = 1 and 3) with six 4-substituted anilines 2, where the 4-substituents are Me, OMe, NO2, Cl, Br, I, in acetonitrile under reflux. © ARKAT USA, Inc.