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

Author(s)

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

Affiliation

^[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

• Document type: Journal article
• Source: MARINE BIOTECHNOLOGY; v. 22, n. 2 MAR 2020.
• Web of Science Citations: 0

Abstract

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)

• FAPESP's process: 14/18257-0 - New approaches in biocatalytic reactions
• Grantee: Andre Luiz Meleiro Porto
• Support Opportunities: Regular Research Grants
• FAPESP's process: 16/20155-7 - Biocatalytic reactions of aminolysis and kinetic resolution by lipases and biodegradation of agrochemicals by microorganisms
• Grantee: Andre Luiz Meleiro Porto
• Support Opportunities: Regular Research Grants