First synthesis of aminonaphthoquinones derived from lawsone in a colloidal dispersion system created by a Brønsted acid-surfactant-combined catalyst in water: An environmentally friendly protocol

Abstract

a b s t r a c tEnvironmentally friendly one-pot protocol was developed for the first synthesis of aminonaphthoquinones derived from 2-hydroxy-1,4-naphthoquinone (lawsone) via a multicomponent Mannich reaction in aqueous media using a catalytic amount of dodecyl benzenesulfonic acid (DBSA), exploring a Brønsted acid-surfactant catalyst (BASC) concept, at room temperature.

A Green Multicomponent Domino Mannich‐Michael Reaction to Synthesize Novel Naphthoquinone‐Polyphenols with Antiproliferative and Antioxidant Activities

“…According to the 1 H NMR, the formation of polyphenol scaffolds was verified through the signals referring to the naphthalenetriol group, in which doublets were assigned around 7.76 and 7.97 ppm, respectively, both integrating for two hydrogens, as expected. Furthermore, the presence of the singlet was verified around 6.70 ppm, referring to the methinic proton characteristic of the Mannich reaction [37,39,40] . Nevertheless, according to the 13 C NMR spectra, carbon signals in the aromatic region were assigned to the carbons of the naphthalenetriol group, based on the correlations found in the HSQC and HMBC spectra (See supplementary material).…”