期刊
MOLECULES
卷 24, 期 5, 页码 -出版社
MDPI
DOI: 10.3390/molecules24050975
关键词
(S)-(-)-perillaldehyde; Ammodaucus leucotrichus; amines; hemi-synthesis; essential oil; 2D NMR; single-crystal X-ray diffraction; chiral-HPLC
资金
- University of Aveiro
- FCT/MEC [FCT UID/QUI/00062/2019, POCI-01-0145-FEDER-007679, UID/CTM/50011/2019]
- FEDER under the PT2020 Partnership Agreement
- [PT-DZ/0005]
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.
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