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一种用于通过多组分串联氧化过程合成2-氨基-3-氰基-4H-色烯的新型贱金属多功能催化剂。

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

作者信息

Chahkamali Farhad Omarzehi, Sobhani Sara, Sansano Jose Miguel

机构信息

Department of Chemistry, College of Sciences, University of Birjand, Birjand, Iran.

Departamento de Química Orgánica, Facultad de Ciencias, Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080, Alicante, Spain.

出版信息

Sci Rep. 2022 Feb 21;12(1):2867. doi: 10.1038/s41598-022-06759-7.

DOI:10.1038/s41598-022-06759-7
PMID:35190576
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8861043/
Abstract

A novel base-metal multifunctional nanomagnetic catalyst is prepared by the immobilization of tungstate anions onto γ-FeO supported with imidazolium moieties. The (γ-FeO-Im-Py)WO 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-4H-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-4H-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.

摘要

通过将钨酸根阴离子固定在负载有咪唑基团的γ-FeO上，制备了一种新型的贱金属多功能纳米磁性催化剂。利用傅里叶变换红外光谱（FT-IR）、X射线光电子能谱（XPS）、透射电子显微镜（TEM）、场发射扫描电子显微镜（FESEM）、电感耦合等离子体质谱（ICP）、热重分析（TGA）、振动样品磁强计（VSM）和X射线衍射（XRD）对（γ-FeO-Im-Py）WO进行了全面表征，并将其用作多功能非均相催化剂，用于在无溶剂条件下通过从醇开始的多组分串联氧化过程合成2-氨基-3-氰基-4H-色烯。在此过程中，钨酸盐在叔丁基过氧化氢（TBHP）作为清洁氧源的存在下催化多种醇的氧化。原位生成的醛通过催化剂的吡啶和咪唑基团促进，与丙二腈和β-二羰基化合物/萘酚/4-羟基香豆素缩合。通过这种方法，以醇作为廉价且易于获得的起始原料，以良好至高收率生成了多种2-氨基-3-氰基-4H-色烯。借助外部磁场可轻松回收催化剂，并在连续五次运行中重复使用，活性无明显下降。

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