Synthesis of new heterocyclics from epoxypulegone

Abstract

Heterocyclic compounds have been widely used in pharmacology. They play the role of precursors for the synthesis of certain drugs. They also have therapeutic and agri-food properties. In our work, we have prepared heterocycles with different chains by condensation of the different nitrogenous reactants on the epoxypulegone. First, we treated a-ketolpulegone, from the epoxypulegone, and the diastereoisomer (1R, 3R) -3,4’dimethylspiro [cyclohexane-1,2’ (1’H)-quinoleine] by m-chloroperbenzoic acid in methylene chloride. We obtained respectively epoxyketol and (1R, 3R)-3,4’dimethylspiro [cyclohexane-1,2’ (1’H)-quinoleine] in good yield. On the other hand, we have prepared new benzodiazepine compounds contiguous to the terpene skeleton of pulegone by condensation of orthophenylenediamine and their derivatives on the epoxypulegone. The products obtained were characterized by spectroscopy IR, 1 H NMR and 13 C NMR.