Cu-Mn Bimetallic Complex Immobilized on Magnetic NPs as an Efficient Catalyst for Domino One-Pot Preparation of Benzimid
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Cu‑Mn Bimetallic Complex Immobilized on Magnetic NPs as an Efficient Catalyst for Domino One‑Pot Preparation of Benzimidazole and Biginelli Reactions from Alcohols Mohammad Ali Nasseri1 · Zinat Rezazadeh1 · Milad Kazemnejadi1 · Ali Allahresani1 Received: 19 May 2020 / Accepted: 28 August 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract An efficient magnetically recyclable bimetallic catalyst by anchoring copper and manganese complexes on the Fe3O4 NPs was prepared and named as Fe3O4@Cu-Mn. It was founded as a powerful catalyst for the domino one-pot oxidative benzimidazole and Biginelli reactions from benzyl alcohols as a green protocol in the presence of air, under solvent-free and mild conditions. Fe3O4@Cu-Mn NPs were well characterized by FT-IR, XRD, FE-SEM, TEM, VSM, TGA, EDX, DLS, and ICP analyses. The optimum range of parameters such as time, temperature, amount of catalyst, and solvent were investigated for the domino one-pot benzimidazole and Biginelli reactions to find the optimum reaction conditions. The catalyst was compatible with a variety of benzyl alcohols, which provides favorable products with good to high yields for all of derivatives. Hot filtration and Hg poisoning tests from the nanocatalyst revealed the stability, low metal leaching and heterogeneous nature of the catalyst. To prove the synergistic and cooperative effect of the catalytic system, the various homologues of the catalyst were prepared and then applied to a model reaction separately. Finally, the catalyst could be filtered from the reaction mixture simply, and reused for five consecutive cycles with a minimum loss in catalytic activity and performance. Graphic Abstract A new magnetically recyclable Cu/Mn bimetallic catalyst has been developed for domino one-pot oxidation-condensation of benzimidazole and Biginelli reactions from alcohols.
Keywords Bimetallic catalyst · Fe3O4@cu-mn · One-pot multicomponent reactions · Benzyl alcohols Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10562-020-03371-0) contains supplementary material, which is available to authorized users. * Mohammad Ali Nasseri [email protected] Extended author information available on the last page of the article
1 Introduction Most sustainable intermediates have resulted from multicomponent reactions as a key synthetic method due to obvious advantages including synthetic efficiency and
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molecular diversity. Among all these type of reactions, Biginelli and benzimidazole reactions were highly regarded due to the most robust biological and therapeutic activities [1, 2]. Dihydropyrimidinones (DHPMs) and their derivatives have been found to revolutionize situation in synthetic methodologies that so-called Biginelli reaction. Biginelli is a cyclo-condensation reaction which synthesized carbonyl components in the strong acidic medium [3–7]. On the other hand, benzimidazoles are heterocyclic aromatic compounds containing fused benzene and imidazole rin
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