American Chemical Society
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Diphenhydramine Hydrochloride–CuCl as a New Catalyst for the Synthesis of Tetrahydrocinnolin-5(1H)‑ones

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journal contribution
posted on 2023-04-28, 17:39 authored by Mehri Moeini Korbekandi, Iraj Mohammadpoor-Baltork, Majid Moghadam, Shahram Tangestaninejad, Valiollah Mirkhani, Akbar Omidvar, Behrouz Notash
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 1H 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(1H)-ones via 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(1H)-one derivatives as well as mono- and bis-tetrahydrocinnolin-5(1H)-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(1H)-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.