Synthesis of New Fluorine-Containing 1,2,3,4-Tetrahydroacridines

Abstract

A convenient method for the synthesis of a novel series of four 5-trilfluoromethyl-1,2,3,4-tetrahydroacridines, by intramolecular cyclization reactions of 2-trifluoroacetyl-1-(arylamino)-cyclohexene using polyphosphoric acid (PPA), is described. The six new enaminoketone intermediates were obtained by an oxygen–nitrogen exchange reaction from 2-trifluoroacetyl-1-methoxycyclohexene with six 4-substituted anilines.

Keywords:

• Acridines
• cyclohexene
• PPA
• tetrahydroacridines

ACKNOWLEDGMENTS

The authors thank Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) for financial support. Fellowships from the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) (T. S. M.) and Fundação de Apoio a Tecnologia e Ciência (FATEC) are also acknowledged.