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Reaction of 3-aminoacridine with formaldehyde in acidic media: access to a series of "fascinating" molecules

A.Tatibouët, M.Demeunynck, J.Lhomme and P.Vatton

LEDSS Université J. Fourier, BP 53, 38041 Grenoble cedex, France

Depending on the nature of the solvent (TFA, MsOH, HCl) and on the stochiometry in formaldehyde, 3-aminoacridine can be selectively transformed into four different types of new heterocyclic structures: a dihydro-oxazine derivative, a tri-aza heptacycle, a dihydroquinazoline derivative and a Tröger's Base analogue.
Some of these compounds are precursors of complex and interesting molecules: DNA intercalating-alkylating agents (quinone -imine-methide precursor), hexa-aza kekulene, poly-aza helicene.