Hemi-Synthesis of Chiral Imine, Benzimidazole and Benzodiazepines from Essential Oil of Ammodaucus leucotrichus subsp. leucotrichus


The hemi-synthesis of chiral imine, benzimidazole and benzodiazepine structures is reported by the condensation of (S)-(-)-perillaldehyde, the major phytochemical of Ammodaucus leucotrichus subsp. leucotrichus essential oil, with different amine derivatives of 2,3-diaminomaleonitrile, o-phenylenediamine and 3-[(2-aminoaryl)amino]dimedone. The reaction proceeds in situ at ambient temperature without prior isolation of the natural (S)-(-)-perillaldehyde. Final products precipitate in the ethanolic reaction medium. 2D NMR and single-crystal X-ray diffraction studies were used to unequivocally characterize the structures in solution and in the solid state, respectively. Chiral HPLC analysis confirms the formation of unique enantiomers and diastereomeric mixtures.



subject category

Biochemistry & Molecular Biology; Chemistry


Chebrouk, F; Madani, K; Cherfaoui, B; Boukenna, L; Valega, M; Mendes, RF; Paz, FAA; Bachari, K; Talhi, O; Silva, AMS

our authors


Thanks are due to University of Aveiro and FCT/MEC for the financial support to the QOPNA research project (FCT UID/QUI/00062/2019), the project CICECO-Aveiro Institute of Materials, POCI-01-0145-FEDER-007679 (FCT Ref. UID/CTM/50011/2019), financed by national funds and when appropriate co-financed by FEDER under the PT2020 Partnership Agreement, and of the bilateral project PT-DZ/0005 and to the Portuguese NMR Network. We would like also to thank the General Directorate for Scientific Research and Technological Development-DGRSDT of Algeria and Agence Thematique de Recherche en Sciences et Technologie ATRST for approving the co-financed bilateral project PT-DZ/0005.

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