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

Publish Year: 1398
نوع سند: مقاله کنفرانسی
زبان: English
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ISOC27_081

تاریخ نمایه سازی: 19 اسفند 1399

Abstract:

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.

Authors

Toktam Shiebani Daloee

Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran

Farahnaz K. Behbahani

Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran