Electrochemical functionalization of quinolizidine alkaloids Raquel Durão, Jaime A. S. Coelho, Svilen. P. Simeonov, Carlos A. M. Afonso University of Lisbon, Portugal Quinolizidine alkaloids (QA) are largely abundant in the Leguminosae family, especially in the genera Lupinus [1]. Maulide and Afonso’s groups developed a process for the extraction of lupanine from Lupinus albus seeds wastewater and the preparation of sparteine [2]. These natural products are known for their pharmacological activities, which includes antimicrobial, antihypertensive, antimuscarinic and antidiabetic, as hyperglycemia agents, effects on the central nervous system and uses in asymmetric organic synthesis [3]. Motivated by the potential added value of novel QA derivatives, we explored the selective C-H functionalization of QA using electrochemistry. Herein we present a new methodology for the cyanation of lupanine (Figure 1), which offers an efficient and greener alternative to conventional methods. The electrochemistry equipment used in this work was an ElectraSyn 2.0 system by IKA.
Figure 1: Electrochemical cyanation methodology. Acknowledgements
We thank the Fundação para a Ciência e a Tecnologia (FCT) for financial support (Ref. 2020/06352/BD, UIDB/04138/2020 and UIDP/04138/2020), COMPETE Programme (SAICTPAC/0019/2015) and PTDC/QUI- QOR/1786/2021. The project leading to this application has received funding from the European Union’s Horizon 2020 research and innovation programme under grant agreement No 951996. J.A.S.C. thanks FCT for Scientific Employment Stimulus 2020/02383/CEECIND. References 1. S. Bunsupa, M. Yamazaki, and K. Saito, Front. Plant Sci. , vol. 3, no. OCT, pp. 1–7, 2012. R. F. M. F. N. Maulide, B. Peng, C. A. M. Afonso, EP2808326A1; WO2014191261A1; 3-12-2013. 2. J. Pothier, S. L. Cheav, N. Galand, C. Dormeau, and C. Viel, J. Pharm. Pharmacol. , vol. 50, no. 8, pp. 949–954, 1998. 3. F. V. Romeo, S. Fabroni, G. Ballistreri, S. Muccilli, A. Spina, and P. Rapisarda, Sustain. , vol. 10, no. 3, pp. 6–10, 2018. 4. M. Wiedemann, C. M. Gurrola-Díaz, B. Vargas-Guerrero, M. Wink, P. M. García-López, and M. Düfer, Molecules , vol. 20, no. 10, pp. 19085–19100, 2015. 5. S. Carmalia, V. D. Alves, I. M. Coelhoso, L. M. Ferreira, and A. M. Lourenço, Sep. Purif. Technol. , vol. 74, no. 1, pp. 38–43, 2010.
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