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Molecules. 2019 Mar 10;24(5). pii: E975. doi: 10.3390/molecules24050975.

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

Author information

1
Laboratory of Biomathematics, Biochemistry, Biophysics and Scientometrics (L3BS), Faculty of Nature and Life Sciences (FSNV), University of Bejaia, 06000 Bejaia, Algeria. chebroukfarid@yahoo.fr.
2
Scientific and Technical Center of Research in Physical and Chemical Analysis CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria. chebroukfarid@yahoo.fr.
3
Laboratory of Biomathematics, Biochemistry, Biophysics and Scientometrics (L3BS), Faculty of Nature and Life Sciences (FSNV), University of Bejaia, 06000 Bejaia, Algeria. khodir.madani@univ-bejaia.dz.
4
Scientific and Technical Center of Research in Physical and Chemical Analysis CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria. cherfaoui.br@gmail.com.
5
Scientific and Technical Center of Research in Physical and Chemical Analysis CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria. lboukenna15@gmail.com.
6
QOPNA and LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal. mvalega@ua.pt.
7
CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal. rfmendes@ua.pt.
8
CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal. filipe.paz@ua.pt.
9
Scientific and Technical Center of Research in Physical and Chemical Analysis CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria. bachari2000@yahoo.fr.
10
Scientific and Technical Center of Research in Physical and Chemical Analysis CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria. oualid.talhi@ua.pt.
11
QOPNA and LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal. oualid.talhi@ua.pt.
12
QOPNA and LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal. artur.silva@ua.pt.

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.

KEYWORDS:

(S)-(−)-perillaldehyde; 2D NMR; Ammodaucus leucotrichus; amines; chiral-HPLC; essential oil; hemi-synthesis; single-crystal X-ray diffraction

PMID:
30857362
PMCID:
PMC6429316
DOI:
10.3390/molecules24050975
[Indexed for MEDLINE]
Free PMC Article

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