1H-imidazol-3-ium tricyanomethanide {[HIM]C(CN)3} as a nanostructured molten salt catalyst: application to the synthesis of pyrano[4,3‐b]pyrans

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Title: 1H-imidazol-3-ium tricyanomethanide {[HIM]C(CN)3} as a nanostructured molten salt catalyst: application to the synthesis of pyrano[4,3‐b]pyrans
Authors: Zolfigol, Mohammad Ali | Yarie, Meysam | Baghery, Saeed | Khoshnood, Abbas | Alonso, Diego A.
Research Group/s: Catálisis Estereoselectiva en Síntesis Orgánica (CESO)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Multicomponent reactions | Knoevenagel condensation | Nanostructured molten salt | Neat conditions | Green chemistry
Knowledge Area: Química Orgánica
Issue Date: May-2017
Publisher: Springer Science+Business Media Dordrecht
Citation: Research on Chemical Intermediates. 2017, 43(5): 3291-3305. doi:10.1007/s11164-016-2826-y
Abstract: In this work, we have synthesized a novel nanostructured molten salt, 1H-imidazol-3-ium tricyanomethanide {[HIMI]C(CN)3} (1), as an efficient and green protocol-compatible catalyst. This new molten salt has been fully characterized by different analytical techniques, such as FT-IR, 1HNMR, 13CNMR, thermal gravimetric analysis, derivative thermal gravimetric analysis, differential thermal analysis, X-ray diffraction, scanning electron microscopy, and high-resolution transmission electron microscopy. Additionally, the catalytic activity of {[HIMI]C(CN)3} (1, 2 mol%) has been tested in a three-component domino Knoevenagel condensation reaction. A range of structurally diverse aromatic aldehydes (2a–p), malononitrile (3), and 4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one (4) are tolerated for the synthesis of 2-amino-7-methyl-5-oxo-4-aryl-4,5-dihydropyrano[4,3-b]pyran-3-carbonitrile derivatives (5a–p) under neat conditions at 50 °C. The obtained results have demonstrated that catalyst 1 shows interesting catalytic properties, such as clean reaction profile, cost-effectiveness, and green conditions. Importantly, the aforementioned catalyst is thermally stable with a 171 °C melting point not showing any significant loss in catalytic activity after 7 reaction cycles.
Sponsor: We thank Bu-Ali Sina University, Iran National Science Foundation (INSF) (Grant of Allameh Tabataba’i’s Award, Grant Number BN093), National Elites Foundation, University of Alicante (VIGROB-173), and the Spanish Ministerio de Economíay Competitividad (CTQ2015-66624-P) for financial support to our research groups.
URI: http://hdl.handle.net/10045/66495
ISSN: 0922-6168 (Print) | 1568-5675 (Online)
DOI: 10.1007/s11164-016-2826-y
Language: eng
Type: info:eu-repo/semantics/article
Rights: © Springer Science+Business Media Dordrecht 2017. The final publication is available at Springer via http://dx.doi.org/10.1007/s11164-016-2826-y
Peer Review: si
Publisher version: http://dx.doi.org/10.1007/s11164-016-2826-y
Appears in Collections:INV - CESO - Artículos de Revistas

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