One-pot three-component synthesis of aminonaphthoquinones derived from lawsone using L-proline as an organocatalyst
Publish place: 27th Iranian Seminar on Organic Chemistry
Publish Year: 1398
نوع سند: مقاله کنفرانسی
زبان: English
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شناسه ملی سند علمی:
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.
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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