Korbekandi Mehri Moeini, Mohammadpoor-Baltork Iraj, Moghadam Majid, Tangestaninejad Shahram, Mirkhani Valiollah, Omidvar Akbar, Notash Behrouz
Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan 81746-73441, Iran.
Department of Physical Chemistry, Faculty of Chemistry, University of Isfahan, Isfahan 81746-73441, Iran.
ACS Omega. 2023 Apr 28;8(18):15883-15895. doi: 10.1021/acsomega.2c06765. eCollection 2023 May 9.
The current study deals with the synthesis and characterization of a novel catalyst made from diphenhydramine hydrochloride and CuCl ([HDPH]Cl-CuCl). The prepared catalyst was thoroughly characterized using various techniques, such as H NMR, Fourier transform-infrared spectroscopy, differential scanning calorimetry, and thermogravimetric analysis and derivative thermogravimetry. More importantly, the observed hydrogen bond between the components was proven experimentally. The activity of this catalyst was checked in the preparation of some new derivatives of tetrahydrocinnolin-5(1)-ones a multicomponent reaction between dimedone, aromatic aldehydes, and aryl/alkyl hydrazines in ethanol as a green solvent. Also, for the first time, this new homogeneous catalytic system was effectively used for the preparation of unsymmetric tetrahydrocinnolin-5(1)-one derivatives as well as - and -tetrahydrocinnolin-5(1)-ones from two different aryl aldehydes and dialdehydes, respectively. The effectiveness of this catalyst was further confirmed by the preparation of compounds containing both tetrahydrocinnolin-5(1)-one and benzimidazole moieties from dialdehydes. The one-pot operation, mild conditions, rapid reaction, and high atom economy, along with the recyclability and reusability of the catalyst, are other notable features of this approach.
本研究涉及由盐酸苯海拉明和氯化铜制备的新型催化剂（[HDPH]Cl-CuCl）的合成与表征。使用多种技术对制备的催化剂进行了全面表征，如氢核磁共振、傅里叶变换红外光谱、差示扫描量热法、热重分析和微商热重分析。更重要的是，通过实验证实了各组分之间存在氢键。在以乙醇为绿色溶剂，由达米酮、芳香醛和芳基/烷基肼进行多组分反应制备一些新的四氢喹唑啉-5(1)-酮衍生物时，对该催化剂的活性进行了检验。此外，这种新型均相催化体系首次有效地用于分别由两种不同的芳醛和二醛制备不对称四氢喹唑啉-5(1)-酮衍生物以及 - 和 -四氢喹唑啉-5(1)-酮。通过由二醛制备同时含有四氢喹唑啉-5(1)-酮和苯并咪唑部分的化合物，进一步证实了该催化剂的有效性。一锅操作、温和的条件、快速的反应、高原子经济性以及催化剂的可回收性和可重复使用性是该方法的其他显著特点。
