Synthesis of Knoevenagel Adducts Under Microwave Irradiation and Biocatalytic Ene-Reduction by the Marine-Derived Fungus Cladosporium sp. CBMAI 1237 for the Production of 2-Cyano-3-Phenylpropanamide Derivatives

Autor(es)

Birolli, Willian Garcia ^{[1, 2]} ; Zanin, Lucas Lima ^[1] ; Jimenez, David Esteban Quintero ^[3] ; Porto, Andre Luiz Meleiro ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, Ave Joao Dagnone 1100, Ed Quim Ambiental, BR-13563120 Sao Carlos, SP - Brazil

^[2] Univ Fed Sao Carlos, Dept Quim, Ctr Ciencias Exatas & Tecnol, Via Washington Luiz, Km 235, Caixa Postal 676, BR-13565905 Sao Carlos, SP - Brazil

^[3] Univ Fed Amapa, Dept Quim, Rod Duca Serra 1233, BR-68925000 Macapa, AP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: MARINE BIOTECHNOLOGY; v. 22, n. 2 MAR 2020.
• Citações Web of Science: 0

Resumo

The organic synthesis has been driven by the need of sustainable processes, which also requires efficiency and cost-effectiveness. In this work, we described the synthesis of nine Knoevenagel adducts between cyanoacetamide and aromatic aldehydes ((E)-2-cyano-3-(phenyl)acrylamide derivatives), employing triethylamine as catalyst under microwave irradiation in 30 min with excellent yields (93-99% yield). Then, these adducts were employed in the C-C double bond bioreduction by the marine-derived fungus Cladosporium sp. CBMAI 1237 for obtention of 2-cyano-3-phenylpropanamide derivatives in mild conditions and short reaction time for a whole-cells reduction (phosphate buffer pH 7.0, 32 degrees C, 130 rpm, 8 h) with good yields (48-90%). It is important to emphasize that the experimental conditions, especially the reaction time, should be carefully evaluated for the obtention of high yields. Since a biodegradation process consumed the obtained product in extended periods, probably due to the use of the substrate as carbon and nitrogen source. This approach showed that the use of coupled and greener catalysis methods such as microwave irradiation and biocatalytic reduction, which employs unique biocatalysts like marine-derived fungi, can be an interesting tool for the obtention of organic molecules. (AU)

• Processo FAPESP: 14/18257-0 - Novas abordagens em reações biocatalíticas
• Beneficiário: Andre Luiz Meleiro Porto
• Linha de fomento: Auxílio à Pesquisa - Regular
• Processo FAPESP: 16/20155-7 - Reações de aminólise e de resolução cinética por lipases e biodegradação de agroquímicos por microrganismos
• Beneficiário: Andre Luiz Meleiro Porto
• Linha de fomento: Auxílio à Pesquisa - Regular