Synthesis of new 2-N,N'-dialkylamino-1,4-naphthoquinone derivatives: Concerning the reactivity of lapachol with secondary amines

Abstract

The reactivity of 2-methoxy-naphthoquinones with secondary amines can be modified by the presence of side-chain substituents in natural and synthetic quinones. We report the synthesis of 2-dialkylamino-1,4-naphthoquinone derivatives by nucleophilic substitution with secondary amines using 2-methoxy-1,4-naphthoquinones derived from nor-lapachol and lawsone. The reported reactions show good yields and straightforward experimental conditions. No products were obtained for the reaction of 2-methoxy-lapachol with secondary amines under the studied experimental conditions. The compounds were characterized by 1 H, 13C NMR spectroscopy, HMBC, IR and by comparing with literature data.