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Efficient and straightforward access to diverse and densely functionalized chromenes by 3-amino-1,2,4-triazole supported on hydroxyapatite-encapsulated- γ-Fe2O3 (γ-Fe2O3@HAp@CPTMS@AT) as a new magnetic basic nanocatalyst

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Abstract

A highly efficient and straightforward one-pot three-component synthesis of functionalized 2-amino-4H-chromenes and indole-substituted 3-amino-1H-benzo[f]chromenes have been developed by 3-amino-1,2,4-triazole supported on hydroxyapatite-encapsulated-γ-Fe2O3 (γ-Fe2O3@HAp@CPTMS@AT) as the new magnetically recyclable heterogeneous basic nanocatalyst. The wide range of valuable 4H-chromene and 1H-chromene structures having different substituents were efficiently synthesized using one-pot tandem Knoevenagel cyclocondensation reaction of aromatic aldehydes, active methylene nitriles (malononitrile and 3-cyanoacetylindole) and diverse phenolic nucleophiles (resorcinol, α-naphthol and β-naphthol) in the presence of nano γ-Fe2O3@HAp@CPTMS@AT in EtOH. The structure and morphology of the synthesized nanocatalyst were characterized by using various techniques such as FT-IR, FESEM, EDS, XRD, TGA-DTA and VSM. The catalytic activity of nano γ-Fe2O3@HAp@CPTMS@AT was evaluated and the results indicated its applicability as a novel, highly efficient, green, recyclable and promising heterogeneous basic nanocatalyst for the synthesis of 4H-chromene and 1H-chromene derivatives.

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Authors are grateful to the Research Council of University of Guilan for the partial financial support of this work.

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  1. Department of Chemistry, Faculty of Sciences, University of Guilan, P.O. Box 41335-1914, Rasht, Iran

    Parivash Jahanshahi & Manouchehr Mamaghani

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  1. Parivash Jahanshahi
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Jahanshahi, P., Mamaghani, M. Efficient and straightforward access to diverse and densely functionalized chromenes by 3-amino-1,2,4-triazole supported on hydroxyapatite-encapsulated- γ-Fe2O3 (γ-Fe2O3@HAp@CPTMS@AT) as a new magnetic basic nanocatalyst. Reac Kinet Mech Cat 130, 955–977 (2020). https://doi.org/10.1007/s11144-020-01825-5

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