A Green and Efficient NH4OAc-catalyzed Synthesis of 2-Hydroxy-3-(arylmethyl)(4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-1,4-naphthoquinones

Abstract

The green and efficient approach for synthesis of 2-hydroxy-3-(arylmethyl)(4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-1,4-naphthoquinones starting from 2-hydroxy-1,4-naphthoquinone, tetronic acid, and aromatic aldehydes was developed. These reactions were carried out in ethanol under microwave irradiation in the presence of ammonium acetate as catalyst. These multicomponent domino reactions presumably occur via NH4OAc-catalyzed Mannich reaction - Michael addition - hydration - tautomerism - elimination sequence of reactions.

The Relevance and Insights on 1,4-Naphthoquinones as Antimicrobial and Antitumoral Molecules: A Systematic Review

“…The synthesis of 3-(aminomethyl)-2-hydroxy-1,4-naphthoquinones through multicomponent reactions with a non-enolizable aldehyde and primary or secondary amines has been reported [20]. Mannich bases with alkyl, aryl, heteroaryl substituents [46][47][48] and copper and vanadium complexes [49,50] have been reported. Giang et al used the Mannich reaction to prepare 3,3'-(arylmethylene)bis(2-hydroxynaphthalene-1,4-diones) and 2-hydroxy-3-(arylmethyl)(4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-1,4-naphthoquinones under microwave irradiation [46,47].…”

“…Mannich bases with alkyl, aryl, heteroaryl substituents [46][47][48] and copper and vanadium complexes [49,50] have been reported. Giang et al used the Mannich reaction to prepare 3,3'-(arylmethylene)bis(2-hydroxynaphthalene-1,4-diones) and 2-hydroxy-3-(arylmethyl)(4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-1,4-naphthoquinones under microwave irradiation [46,47]. Furthermore, naphthoquinone-1H-1,2,3-triazoles derivatives have been prepared by oxidative cycloaddition between lawsone and 4-vinyl-1H-1,2,3triazoles; then, reductive acetylation helped to obtain dihydronaphthofurandiyl diacetates in good yields [48] (Figure 8).…”