Hemi-Synthesis of Chiral Imine, Benzimidazole and Benzodiazepines from Essential Oil of Ammodaucus leucotrichus subsp. leucotrichus
Farid Chebrouk,
Khodir Madani,
Brahim Cherfaoui,
Leila Boukenna,
Mónica Válega,
Ricardo F. Mendes,
Filipe A. A. Paz,
Khaldoun Bachari,
Oualid Talhi,
Artur M. S. Silva
Affiliations
Farid Chebrouk
Laboratory of Biomathematics, Biochemistry, Biophysics and Scientometrics (L3BS), Faculty of Nature and Life Sciences (FSNV), University of Bejaia, 06000 Bejaia, Algeria
Khodir Madani
Laboratory of Biomathematics, Biochemistry, Biophysics and Scientometrics (L3BS), Faculty of Nature and Life Sciences (FSNV), University of Bejaia, 06000 Bejaia, Algeria
Brahim Cherfaoui
Scientific and Technical Center of Research in Physical and Chemical Analysis CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria
Leila Boukenna
Scientific and Technical Center of Research in Physical and Chemical Analysis CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria
Mónica Válega
QOPNA and LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Ricardo F. Mendes
CICECO—Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Filipe A. A. Paz
CICECO—Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Khaldoun Bachari
Scientific and Technical Center of Research in Physical and Chemical Analysis CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria
Oualid Talhi
Scientific and Technical Center of Research in Physical and Chemical Analysis CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria
Artur M. S. Silva
QOPNA and LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
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.
