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从精油中半合成新型手性苯并二氮杂卓衍生物:非对映异构体的二维 NMR 实验和差示扫描量热法研究。

Hemi-synthesis of novel chiral benzodiazepine derivatives from essential oil: 2D NMR experiments and differential scanning calorimetry study of diastereoisomers.

机构信息

Scientific and Technical Center of Research in Physical and Chemical Analysis CRAPC, BP384, Tipaza, Algeria.

Laboratory of Polymeric Materials (LPM), Faculty of Chemistry, U.S.T.H.B., Algiers, Algeria.

出版信息

Nat Prod Res. 2024 Jul;38(14):2486-2497. doi: 10.1080/14786419.2023.2185888. Epub 2023 Mar 8.

DOI:10.1080/14786419.2023.2185888
PMID:36890766
Abstract

An efficient condensation of citronellal, the main constituent of essential oil (51%), with different amine derivatives of 2,3-diaminomaleonitrile and 3-[(2-aminoaryl)amino]dimedone has led to novel chiral benzodiazepine structures. All reactions were precipitated in ethanol and pure products were obtained in good yields (58-75%) without any purification. The synthesized benezodiazepines were characterized by spectroscopic techniques, namely H-NMR, C-NMR, 2D NMR and FTIR. Differential Scanning Calorimetry (DSC) and HPLC were used to confirm the formation diastereomeric mixtures of benzodiazepine derivatives.

摘要

柠檬醛是一种主要的精油成分(51%),与 2,3-二氨基马来腈和 3-[(2-氨基芳基)氨基]二亚甲基酮的不同胺衍生物的高效缩合,导致了新型手性苯并二氮杂䓬结构的形成。所有反应都在乙醇中沉淀,并且在没有任何纯化的情况下,以良好的收率(58-75%)得到了纯产物。所合成的苯并二氮杂䓬通过光谱技术,即 H-NMR、C-NMR、2D NMR 和 FTIR 进行了表征。差示扫描量热法(DSC)和 HPLC 用于确认苯并二氮杂䓬衍生物的非对映异构体混合物的形成。

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