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Molecules 2019, 24(5), 975; https://doi.org/10.3390/molecules24050975

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

1
Laboratory of Biomathematics, Biochemistry, Biophysics and Scientometrics (L3BS), Faculty of Nature and Life Sciences (FSNV), University of Bejaia, 06000 Bejaia, Algeria
2
Research Center Scientific and Technical in Analyzes Physico-Chimiques CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria
3
QOPNA and LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
4
CICECO—Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
5
Laboratory of Applied Organic Chemistry, Faculty of Chemistry, University of Science and Technology Houari Boumediene, BP 32, Alia Bab-Ezzouar, 16111 Algiers, Algeria
*
Authors to whom correspondence should be addressed.
Academic Editor: Maria Elizabeth Tiritan
Received: 27 January 2019 / Revised: 20 February 2019 / Accepted: 6 March 2019 / Published: 10 March 2019
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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. View Full-Text
Keywords: (S)-(−)-perillaldehyde; Ammodaucus leucotrichus; amines; hemi-synthesis; essential oil; 2D NMR; single-crystal X-ray diffraction; chiral-HPLC (S)-(−)-perillaldehyde; Ammodaucus leucotrichus; amines; hemi-synthesis; essential oil; 2D NMR; single-crystal X-ray diffraction; chiral-HPLC
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Chebrouk, F.; Madani, K.; Cherfaoui, B.; Boukenna, L.; Válega, M.; Mendes, R.F.; Paz, F.A.A.; Bachari, K.; Talhi, O.; Silva, A.M.S. Hemi-Synthesis of Chiral Imine, Benzimidazole and Benzodiazepines from Essential Oil of Ammodaucus leucotrichus subsp. leucotrichus. Molecules 2019, 24, 975.

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