Laboratory of Biomathematics, Biochemistry, Biophysics and Scientometrics (L3BS), Faculty of Nature and Life Sciences (FSNV), University of Bejaia, 06000 Bejaia, Algeria.
Scientific and Technical Center of Research in Physical and Chemical Analysis CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria.
Molecules. 2019 Mar 10;24(5):975. doi: 10.3390/molecules24050975.
The hemi-synthesis of chiral imine, benzimidazole and benzodiazepine structures is reported by the condensation of ()-(-)-perillaldehyde, the major phytochemical of subsp. essential oil, with different amine derivatives of 2,3-diaminomaleonitrile, -phenylenediamine and 3-[(2-aminoaryl)amino]dimedone. The reaction proceeds in situ at ambient temperature without prior isolation of the natural ()-(-)-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.
（-）-（-）-紫苏醛与不同的 2,3-二氨基马来腈、-苯二胺和 3-[(2-芳氨基)氨基]二亚甲基酮的胺衍生物缩合，报告了手性亚胺、苯并咪唑和苯并二氮杂结构的半合成。反应在环境温度下就地进行，无需预先分离天然（-）-（-）-紫苏醛。最终产物在乙醇反应介质中沉淀。二维 NMR 和单晶 X 射线衍射研究分别用于在溶液中和固态中明确地确定结构。手性 HPLC 分析证实了独特的对映异构体和非对映异构体混合物的形成。
