Catalytic synthesis of coumarin-linked nicotinonitrile derivatives via a cooperative vinylogous anomeric-based oxidation
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Catalytic synthesis of coumarin‑linked nicotinonitrile derivatives via a cooperative vinylogous anomeric‑based oxidation Morteza Torabi1 · Meysam Yarie1 · Fatemeh Karimi1 · Mohammad Ali Zolfigol1 Received: 18 May 2020 / Accepted: 3 September 2020 © Springer Nature B.V. 2020
Abstract In the presented study, we developed a new and efficient strategy for the synthesis of coumarin-linked nicotinonitrile derivatives via a cooperative vinylogous anomericbased oxidation mechanism. Target compounds were prepared through a four component reaction between aldehyde derivatives, 2-acetyl-3H-benzo[f]chromen-3-one or 3-acetylcoumarin, malononitrile or ethyl cyanoacetate and ammonium acetate, in the presence a catalytic amount of Fe3O4@SiO2@(CH2)3‐urea‐benzimidazole with sulfonic acid tags as a recoverable nanomagnetic catalyst. All reactions proceed smoothly with good to high yields under solvent free conditions.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116 4-020-04267-9) contains supplementary material, which is available to authorized users. * Mohammad Ali Zolfigol [email protected] 1
Department of Organic Chemistry, Faculty of Chemistry, Bu‐Ali Sina University, 6517838683 Hamedan, Iran
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Graphic abstract Fe3O4@SiO2@(CH2)3‐urea‐benzimidazole with sulfonic acid tags shows elegant catalytic activity for the preparation of coumarin linked nicotinonitrile derivateives via a cooperative vinylogous anomeric based oxidation mechanism.
Keywords Coumarin-linked nicotinonitrile · Cooperative vinylogous anomericbased oxidation · Multi-component reaction · Nanomagnetic catalyst
Introduction Over the last decade, much effort has been made to achieve the concept of "ideal synthesis" by chemists. Through ideal synthesis, the target molecule, prepared via a single step and one pot manner by applying readily available starting materials without any side-product formation (100% yield). Ideal synthesis is an environmentally friendly, resource effective, simple, safe and economically acceptable protocol [1, 2]. In terms of concept, one of the closest methods to "ideal synthesis" is multi-component reactions (MCRs) strategy, which covers several aspects of it [3]. MCRs, as an important class of Scheme 1 Hidden ionicity in N-(chloromethyl)piperidine due to anomeric effect
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Catalytic synthesis of coumarin-linked nicotinonitrile… Scheme 2 Vinylogous anomeric effect operates in the exocyclic π-systems
chemical transformations, incorporate three or more starting materials for the synthesis of complex molecule through a low synthetic cost and high atom economy procedure [4]. The concept of MCRs is well reviewed [5–12]. Construction of catalytic systems which displays high activity and selectivity (such as homogeneous catalysts) and possesses the easy separation and reusability (such as heterogeneous catalysts) has become a hot research topic in the domain of modern organic synthesis [13]. By applying magnetic nanoparticles in the pr
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