1. Hemi-Synthesis of Chiral Imine, Benzimidazole and Benzodiazepines from Essential Oil of Ammodaucus leucotrichus subsp. leucotrichus.
- Author
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Chebrouk, Farid, Madani, Khodir, Cherfaoui, Brahim, Boukenna, Leila, Válega, Mónica, Mendes, Ricardo F., Paz, Filipe A. A., Bachari, Khaldoun, Talhi, Oualid, Silva, Artur M. S., and Tiritan, Maria Elizabeth
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CHIRALITY , *IMINES , *BENZIMIDAZOLES , *BENZODIAZEPINES , *ESSENTIAL oils - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2019
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