Details

Autor(en) / Beteiligte

• Terra, Bruna
• Osorio, Aura
• de Oliveira, Aline
• Santos, Rebeca
• Mouro, Andressa
• de Araújo, Natália
• da Silva, Cameron
• Martins, Felipe
• Vieira, Luciene
• Bonaventura, Daniella
• de Abreu, Heitor
• Alcântara, Antonio
• de Fátima, Ângelo

Titel

Natural Organic Acid as Green Catalyst for Xanthenones Synthesis: Methodology, Mechanism and Calcium Channel Blocking Activity

Ist Teil von

• Journal of the Brazilian Chemical Society, 2017-12, Vol.28 (12), p.2313-2325

Ort / Verlag

Sociedade Brasileira de Química

Erscheinungsjahr

2017

Quelle

EZB Electronic Journals Library

Beschreibungen/Notizen

• Xanthenones were synthesized via one-pot tricomponent reaction, under solvent-free conditions, using aldehydes, phenolic and cyclic 1,3-dicarbonyl compounds. Natural organic acids (NOAs), compounds present in many living metabolisms, were used as potential green catalysts. NOA are considered to be more eco-friendly and user-friendly alternative to traditional methodologies. Optimization studies showed that oxalic acid was the best NOA catalyst for such reaction furnishing the xanthenones with up to 93% of yield. Theoretical calculations were performed to evaluate this reaction mechanism and regioselectivity. The results showed that the regiospecificity of this three-component reaction is kinetically and thermodynamically controlled by the addition of β-naphthol C2, instead of C10, to the aldehyde. Our results also disclosed two xanthenones as novel calcium channels blockers. Eco-friendly reaction conditions, easy workup procedure, short reaction times and good yields are some of the advantages of our methodology.