Hmaimou Samir, Ait Lahcen Marouane, Adardour Mohamed, Alanazi Mohammed M, Kabra Atul, Maatallah Mohamed, Baouid Abdesselam
Molecular Chemistry Laboratory, Department of Chemistry, Semlalia Faculty of Sciences, Cadi Ayyad University, Marrakech 40001, Morocco.
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia.
Molecules. 2024 Sep 12;29(18):4323. doi: 10.3390/molecules29184323.
The stereoisomers (E)-2,2-dimethyl-4-(4-subsitutedstyryl)-2,3-dihydro-1H-[1,5]-benzodiazepine were synthesized via the condensation reaction of 2,2,4-trimethyl-2,3-dihydro-1H-1,5-benzodiazepine (BZD) with the benzaldehyde derivatives in ethanol. The chemical structure of the prepared products was confirmed by NMR (H and C), HRMS, and X-ray analysis of the crystal structure . The condensation reaction was examined using DFT calculations at the theoretical level of B3LYP/6-31G(d) to elucidate the chemo-, regio-, and stereoselectivity and the reaction mechanism of the produced isomer. Furthermore, we identified each reagent's reactive sites by the measurement of the reactivity indices. We also looked at how the electron-withdrawing groups (EWGs) of various aldehydes affected the reaction's mechanism and the stability of products .
通过2,2,4-三甲基-2,3-二氢-1H-1,5-苯并二氮杂䓬（BZD）与苯甲醛衍生物在乙醇中发生缩合反应，合成了立体异构体（E）-2,2-二甲基-4-（4-取代苯乙烯基）-2,3-二氢-1H-[1,5]-苯并二氮杂䓬。通过核磁共振（氢谱和碳谱）、高分辨质谱以及产物晶体结构的X射线分析确定了所制备产物的化学结构。在B3LYP/6-31G(d)理论水平上使用密度泛函理论（DFT）计算研究了缩合反应，以阐明化学选择性、区域选择性和立体选择性以及所生成异构体的反应机理。此外，通过测量反应活性指数确定了每种试剂的反应位点。我们还研究了各种醛的吸电子基团（EWG）如何影响反应机理和产物的稳定性。
