A novel base-metal multifunctional catalyst for the synthesis of 2-amino-3-cyano-4H-chromenes by a multicomponent tandem oxidation process

Новый многофункциональный катализатор на основе легкоплавкого металла для синтеза 2-амино-3-циано-4H-хроменов методом многокомпонентного тандемного окисления
José M. Sansano, Sara Sobhani, Farhad Omarzehi Chahkamali
2022-02-21

2-amino-3-cyano-4H-chromenesbase-metal multifunctional catalystmagnetic heterogeneous catalystmulticomponent tandem oxidationtungstate-catalyzed alcohol oxidation
Abstract A novel base-metal multifunctional nanomagnetic catalyst is prepared by the immobilization of tungstate anions onto γ-Fe 2 O 3 supported with imidazolium moieties. The (γ-Fe 2 O 3 -Im-Py) 2 WO 4 was fully characterized using FT-IR, XPS, TEM, FESEM, ICP, TGA, VSM and XRD and used as a multifunctional heterogeneous catalyst for the synthesis of 2-amino-3-cyano-4 H -chromenes via a multicomponent tandem oxidation process starting from alcohols under solvent-free conditions. During this process, tungstate catalyzes the oxidation of a wide range of alcohols in the presence of TBHP as a clean source. The in-situ formed aldehydes are condensed with malononitrile and β-dicarbonyl compounds/naphthols/4-hydroxycumarin through promotion by pyridine and imidazolium moieties of the catalyst. By this method, a variety of 2-amino-3-cyano-4 H -chromenes are generated in good to high yields from alcohols as inexpensive and easily available starting materials. The catalyst is recovered easily by the aid of an external magnetic field and reused in five successive runs with insignificant decreasing activity.
1
A novel base-metal multifunctional heterogeneous catalyst was synthesized and fully characterized (FT-IR, XPS, TEM, FESEM, ICP, TGA, VSM, XRD).
2
Pyridine and imidazolium moieties on the catalyst promote condensation of in-situ aldehydes with malononitrile and β-dicarbonyls/naphthols/4-hydroxycoumarin to form the chromenes.
3
The catalyst enables synthesis of 2-amino-3-cyano-4H-chromenes from alcohols via a multicomponent tandem oxidation process under solvent-free conditions.
4
The catalyst is magnetically recoverable and can be reused for five successive runs with only insignificant loss of activity, delivering good to high yields from inexpensive alcohol starting materials.
5
Tungstate sites on the catalyst oxidize a wide range of alcohols using TBHP, generating in-situ aldehydes for subsequent condensation reactions.

Novel base-metal multifunctional heterogeneous catalyst (magnetically recoverable, containing tungstate, pyridine and imidazolium moieties)

Catalytic performance for synthesizing 2-amino-3-cyano-4H-chromenes from alcohols via a multicomponent tandem oxidation–condensation process (oxidation of alcohols by tungstate/TBHP, in‑situ aldehyde formation and condensation with malononitrile and β-dicarbonyls/naphthols/4-hydroxycoumarin), including recoverability and reusability

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2022-02-21
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Authors
José M. Sansano
Sara Sobhani
Farhad Omarzehi Chahkamali
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