Synthesis and conformational study of acridine derivatives related to 1,4-dihydropyridines

Novel acridine derivatives have been synthesized from dimedone and different aromatic aldehydes by following the classical Hantzsch's procedure. The particular substitution pattern of these compounds is responsible for the observed strong push-pull effect. Quantum chemical calculations were carried out on these molecules by using the AM1 method with complete geometry optimization. The calculated heats of formation reveal two equally favoured conformations. The parameter of planarity and the charge density calculations are in agreement with the ¹³C nmr spectroscopic data.