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Facile and highly diastereo and regioselective synthesis of novel octahydroacridine-isoxazole and octahydroacridine-1,2,3-triazole molecular hybrids from citronella essential oil

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Abstract

A novel and highly efficient synthetic approach for the expedite construction of new octahydroacridine-isoxazole- and octahydroacridine-1,2,3-triazole-based molecular hybrids is first reported. Rapid access to the octahydroacridine core was achieved in a highly diastereoselective fashion via cationic Povarov reaction of N-propargyl anilines and citronella essential oil (Cymbopogon nardus). The subsequent 1,3-dipolar and Cu (I) catalyzed alkyne-azide cycloaddition reaction of the terminal alkyne fragment with the corresponding oxime or azide affords the desired 3,5-isoxazoles and 1,2,3-triazoles, respectively, as interesting molecular hybrid models for pharmacological studies.

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Acknowledgements

This work was supported by Patrimonio Autónomo Fondo Nacional de Financiamiento para la Ciencia, la Tecnología y la Innovación, Francisco José de Caldas (Contract RC-0572-2012). We want to thank Laboratorio de Espectrometria de Masas—Parque Tecnológico Guatiguará for data collection. We also wish to acknowledge Prof. Elena E. Stashenko, Research Director CROM-MASS–CENIVAM, Industrial University of Santander, Colombia, for the generous donation and characterization of the EO of citronella.

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Authors and Affiliations

  1. Laboratorio de Química Orgánica y Biomolecular (LQOBio), CMN, Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 Vía Refugio, Piedecuesta, 681011, Colombia

    Mauricio Acelas & Vladimir V. Kouznetsov

  2. Grupo de Investigación en Compuestos Orgánicos de Interés Medicinal (CODEIM), Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 Vía Refugio, Piedecuesta, 681011, Colombia

    Arnold R. Romero Bohórquez

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  1. Mauricio Acelas
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Correspondence to Arnold R. Romero Bohórquez.

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Acelas, M., Kouznetsov, V.V. & Romero Bohórquez, A.R. Facile and highly diastereo and regioselective synthesis of novel octahydroacridine-isoxazole and octahydroacridine-1,2,3-triazole molecular hybrids from citronella essential oil. Mol Divers 23, 183–193 (2019). https://doi.org/10.1007/s11030-018-9863-y

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