Síntese de novos adutos de lapachol com aminas alifáticas

Abstract

In this work a series of novel lapachol adducts with aliphatic primary amines were synthesized. These amines included 2-aminoethanol, 3-amino-1-propanol, 2- methoxy-ethylamine, 3-methoxy-propylamine, n-butylamine and glycine. All reactions were performed under ambient temperature and without solvents. The newly products with unique structures were characterized by IR and UV spectroscopy and 1H and 13C NMR with bi-dimensional techniques. A possible mechanism was proposed based on the ability of the quinones to react as radical species, where a initially formed imine act as a nucleophile with a second molecule of lapachol, and this primary adduct results in observed products under the oxidant conditions used in reaction. To test this hypothesis the reaction was conducted in inert atmosphere or in the presence of an antioxidant (BHT), and the reaction mixture behaves differently, as expected.