One-pot three-component synthesis of aminonaphthoquinones derived from lawsone using L-proline as an organocatalyst

In regard to biological properties, the pharmacophoric quinone group receives great attention due to its extensive use and its presence in compounds with confirmed antitumour, molluscicidal, leishmanicidal, anti-inflammatory and antifungal activities,1-2 as well as its industrial applications and their potential as intermediates in the synthesis of heterocyclic compounds. Lawsone is a p-naphthoquinone containing an enol group, which is susceptible to a multicomponent Mannich reaction.In this study, environmentally 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 L-proline in refluxing ethanol (Fig.1)The main advantages of the present synthetic protocol are eco-friendly catalyst, easy reaction work-up procedure and precedent some new derivative compounds. The system chosen for the multicomponent Mannich reaction is nontoxic and extremely inexpensive, which aligns with the concept of green chemistry.

کلیدواژه ها:

Lawsone ، L-proline ، Naphthoquinone