Synthesis and Catalytic Application of Bimetallic and Trimetallic Magnetic Nanoalloys for the Preparation of Bis(indolyl
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ynthesis and Catalytic Application of Bimetallic and Trimetallic Magnetic Nanoalloys for the Preparation of Bis(indolyl)methanes K. P. Boroujenia,*, M. Shahrokha, K. Kiania, A. Farokhniaa, R. Kazemia, and F. Kheirib a b
Department of Chemistry, Shahrekord University, Shahrekord, 88186-34141 Iran
Department of Physics, Shahrekord Branch, Islamic Azad University, Shahrekord, 88137-33395 Iran *e-mail: [email protected] Received June 9, 2020; revised June 21, 2020; accepted June 26, 2020
Abstract—Some bimetallic and trimetallic magnetic nanoalloys based on cobalt, copper, and silver have been synthesized and used as and green catalysts for the preparation of bis(indolyl)methanes through electrophilic substitution reaction of indole with carbonyl compounds. The obtained nanoalloys retained their catalytic activity after several reaction cycles. Rietveld analysis of the X-ray powder diffraction patterns revealed the expected Co11.05Cu20.08Ag68.87 ratio in the Co–Cu–Ag nanoalloy. Keywords: magnetic nanoalloys, bis(indolyl)methanes, catalysis, aldehyde
DOI: 10.1134/S1070428020100255 Nowadays nanoalloys are the most attractive subjects of chemical research because of their remarkable properties [1, 2] which can be very unique and completely different from those of their components [3, 4]. Nanoalloys have a high surface-to-volume ratio and exhibit a quantum confinement effect, so they can provide a broad spectrum of magnetic, electrical, thermal, and chemical properties with wide applications in catalysis, electrochemical sensing and biosensing, and medicinal chemistry [5–7]. Among these, bimetallic alloy nanoparticles of Co, Cu, or Ag have been well-established as catalysts or reagents in various chemical transformations such as ethylene epoxidation [8], electrocatalytic reduction of benzyl chloride [9], oxygen reduction reactions [10], oxidation of formaldehyde [11], synthesis of vertically aligned carbon nanofibers [12], methane decomposition [13], hydrolytic dehydrogenation of ammonia-borane [14], hydrogen evolution reactions [15], giant magnetoresistance (GMR) in granular materials [16], thermal decomposition of ammonium perchlorate [17], as antibacterial agents [18], and in the preparation of 1,8-dioxooctahydroxanthenes [19] and biscoumarins [20] along with anti-bacterial, anti-oxidant, and DNA cleavage properties. Indole derivatives are common secondary metabolites from plants, marine natural sources, microorganisms, and other sources [21]. For example, 3,3-bis(1H-indol-3-yl)butane-2-one (I, Scheme 1) [22],
1,1,3-tris(1H-indol-3-yl)butane (II) [22], 2,5-bis(1Hindol-3-ylmethyl)pyrazine (III) [23], and tryptamine isovalerate (IV) [23] have been isolated from microorganisms. Among various indole derivatives, bis(indolyl)methanes (BIMs) in which two indolyl moieties are connected to each other by a carbon atom are known as effective biologically active molecules used as analgesic [24], antifungal [25, 26], and anti-inflammatory agents [27]. Anti-cancer effect of 1,1,3-tri(1Hindol-3-yl)cyclohexane (V) in various lun
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