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