Natural organic acid as green catalyst for xanthenones synthesis: methodology, mechanism and calcium channel blocking activity
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2017
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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 b-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.
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Xanthenones, Natural organic acid, Theoretical calculations, Calcium channels blockers
Citação
TERRA, Bruna S. et al. Natural organic acid as green catalyst for xanthenones synthesis: methodology, mechanism and calcium channel blocking activity. Journal of the Brazilian Chemical Society, Campinas, v. 28, n. 12, p. 2313-2325, 2017. DOI: 10.21577/0103-5053.20170082. Disponível em: https://jbcs.sbq.org.br/default.asp?ed=260. Acesso em: 30 nov. 2023.