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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

  • Mauricio Acelas
  • Vladimir V. Kouznetsov
  • Arnold R. Romero Bohórquez
Original Article

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.

Keywords

Octahydroacridines Isoxazoles Triazoles Molecular hybrids Cationic Povarov reaction Citronella essential oil 

Notes

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.

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

Supplementary material

11030_2018_9863_MOESM1_ESM.docx (3.1 mb)
Supplementary material 1 (DOCX 3218 kb)

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Copyright information

© Springer Nature Switzerland AG 2018

Authors and Affiliations

  • Mauricio Acelas
    • 1
  • Vladimir V. Kouznetsov
    • 1
  • Arnold R. Romero Bohórquez
    • 2
  1. 1.Laboratorio de Química Orgánica y Biomolecular (LQOBio), CMNUniversidad Industrial de Santander, Parque Tecnológico GuatiguaráPiedecuestaColombia
  2. 2.Grupo de Investigación en Compuestos Orgánicos de Interés Medicinal (CODEIM)Universidad Industrial de Santander, Parque Tecnológico GuatiguaráPiedecuestaColombia

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