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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

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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 °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.

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Acknowledgments

The authors thank all the support of the Chemical Analysis Center (São Carlos Institute of Chemistry, University of São Paulo) for the NMR analyses. WGB would like to thanks FAPESP for his post-doctoral scholarship (2017/19721-0).

Funding

This study was financed by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES, Finance Code 001), Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP, 2016/20155-7 and 2014/18257-0) and Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, 302528/2017-2).

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Authors and Affiliations

  1. Instituto de Química de São Carlos, Universidade de São Paulo, Av. João Dagnone, 1100, Ed. Química Ambiental, J. Santa Angelina, São Carlos, SP, 13563-120, Brazil

    Willian Garcia Birolli, Lucas Lima Zanin & André Luiz Meleiro Porto

  2. Departamento de Química, Centro de Ciências Exatas e de Tecnologia, Universidade Federal de São Carlos, Via Washington Luiz, km 235, Caixa Postal 676, São Carlos, SP, 13565-905, Brazil

    Willian Garcia Birolli

  3. Departamento de Química, Universidade Federal do Amapá, Rod. Duca Serra 1233, Bairro Fonte Nova Santana, Macapá, AP, 68925-000, Brazil

    David Esteban Quintero Jimenez

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  1. Willian Garcia Birolli
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  2. Lucas Lima Zanin
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  3. David Esteban Quintero Jimenez
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  4. André Luiz Meleiro Porto
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Correspondence to Willian Garcia Birolli or André Luiz Meleiro Porto.

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Birolli, W.G., Zanin, L.L., Jimenez, D.E.Q. et al. 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. Mar Biotechnol 22, 317–330 (2020). https://doi.org/10.1007/s10126-020-09953-8

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