Hemi-Synthesis of Chiral Imine, Benzimidazole and Benzodiazepines from Essential Oil of Ammodaucus leucotrichus subsp. leucotrichus
authors Chebrouk, F; Madani, K; Cherfaoui, B; Boukenna, L; Valega, M; Mendes, RF; Paz, FAA; Bachari, K; Talhi, O; Silva, AMS
nationality International
author keywords (S)-(-)-perillaldehyde; Ammodaucus leucotrichus; amines; hemi-synthesis; essential oil; 2D NMR; single-crystal X-ray diffraction; chiral-HPLC
abstract 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.
publisher MDPI
issn 1420-3049
year published 2019
volume 24
issue 5
digital object identifier (doi) 10.3390/molecules24050975
web of science category Biochemistry & Molecular Biology; Chemistry, Multidisciplinary
subject category Biochemistry & Molecular Biology; Chemistry
unique article identifier WOS:000462662900151
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