14002-91-6Relevant academic research and scientific papers
Preparation of a novel, efficient, and recyclable magnetic catalyst, Cu(II)-OHPC-Fe3O4 nanoparticles, and a solvent-free protocol for the synthesis of coumarin derivatives
Yuan, Jingjing,Mohammadnia, Majid
, p. 2327 - 2343 (2021/07/26)
Cu(II) supported on 5-oxo-4,5-dihydro-pyrrole-3-carboxylic acid functionalized Fe3O4 nanoparticles (Cu(II)-OHPC-Fe3O4) as a new magnetic nanocatalyst was prepared and characterized by ICP-AES, FT-IR, XRD, SEM, TEM, TGA, XRD, VSM and EDX techniques. Prepared nanocatalyst (Cu(II)-OHPC-Fe3O4) is employed for Pechmann reactions between different substituted phenols and ethyl acetoacetate to obtain new products of coumarin derivatives in good to excellent yields. This green catalyst was easily removed, reused several times with no significant loss of its activity and provided clean synthesis with excellent yield and reduced time.
Recyclable cellulose nanocrystal supported Palladium nanoparticles as an efficient heterogeneous catalyst for the solvent-free synthesis of coumarin derivatives via von Pechmann condensation
Mirosanloo, Atieh,Zareyee, Daryoush,Khalilzadeh, Mohammad A.
, (2018/10/15)
2-Amino pyrimidine nanocellulose-supported Palladium nanoparticles (CNC-AMPD-Pd) as a novel bio supported nanocatalyst was prepared and characterized by ICP-AES, FT-IR, XRD, SEM, TEM, TGA and EDX techniques. The nanocatalyst demonstrated outstanding performance in Pechmann condensation between different substituted phenols and ethyl acetoacetate to obtain coumarin derivatives in good to excellent yields. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst and solvent-free reaction conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup.
A solvent-free synthesis of coumarins using 1,3-disulfonic acid imidazolium hydrogen sulfate as a reusable and effective ionic liquid catalyst
Shirini, Farhad,Yahyazadeh, Asieh,Mohammadi, Kamal
, p. 6207 - 6218 (2015/08/18)
Abstract 1,3-Disulfonic acid imidazolium hydrogen sulfate has been used as an effective and reusable ionic liquid catalyst for the synthesis of coumarins from phenol derivatives with β-ketoesters via the Von Pechmann condensation under solvent-free conditions. This method consistently has the advantages of excellent yields, easy and quick isolation of the products, short reaction times, and green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be recovered and reused for four times without loss of activity.
Sulfonated core-shell magnetic nanoparticle (Fe3O4@SiO2@PrSO3H) as a highly active and durable protonic acid catalyst; Synthesis of coumarin derivatives through pechmann reaction
Esfahani, Farhad Kabiri,Zareyee, Daryoush,Yousefi, Reza
, p. 3333 - 3337 (2015/04/16)
Sulfonic acid supported silica coated magnetic nanoparticles (Fe3O4@SiO2@PrSO3H), was prepared by using low cost precursors and a facile immobilization technique. The final catalyst, which was characterized by XRD, FT-IR, vibrating sample magnetometer (VSM), TEM, and TGA techniques, was found to be an efficient and environmentally benign solid acid for the Pechmann condensation of substituted phenols with ethyl acetoacetate leading to the formation of coumarin derivatives. After the reaction, the catalyst could be effortlessly separated by external magnet and reused for 22 consecutive runs, without any significant loss in catalytic efficiency. The catalytic system presented offers a reusable strategy for the efficient synthesis of coumarin, simplicity in operation, and a green reaction profile by avoiding toxic conventional catalysts and solvents. Green earth and blue sky: Herein, we wish to disclose a simple bench top procedure for the synthesis of sulfonated core-shell magnetic nanoparticles (SMNPs) (Fe3O4@SiO2@PrSO3H) and discuss its performance as a very strong solid acid in the Pechmann condensation reaction.
Synthesis and heterogeneous catalytic activity of covalently immobilized hexamine cation as a magnetically-recoverable nanocatalyst
Kangari, Sahar,Yavari, Issa,Maasoumi, Bakhshali
, p. 1771 - 1779 (2015/08/06)
Functionalized magnetic core-shell nanoparticles Fe3O4-SiO2-HMTA are prepared by co-precipitation method and characterized by SEM, TEM, FT-IR, XRD, and VSM. The particles are spherical with an average size of approximately 48 nm. The catalytic activity of these nanoparticles was tested in solvent-free synthesis of coumarin derivatives. The catalyst was readily recycled by the use of an external magnetic field and can be reused four times without significant loss of activity or mass.
Recyclable CMK-5 supported sulfonic acid as an environmentally benign catalyst for solvent-free one-pot construction of coumarin through Pechmann condensation
Zareyee, Daryoush,Serehneh, Mahshad
, p. 88 - 91 (2014/05/20)
Sulfonic acid modified nanostructured CMK-5 is used as an alternative to conventional acid catalysts in the von Pechmann condensation of a neat mixture of substituted phenols with ethyl acetoacetate leading to the formation of coumarin derivatives at 130 °C. In comparison, CMK-5-SO3H showed a greater activity than some other homogeneous and heterogeneous catalysts. Additionally, the catalyst is reused repeatedly for 6 reaction cycles without any evidence of loss of activity, confirming the stability of the covalent bonding of acidic centers. The methodology presented offers reusable strategy for the efficient synthesis of coumarin, simplicity in operation, and green aspects by avoiding toxic conventional catalysts and solvents.
Diazabicyclo[2.2.2]octane stabilized on Fe3O4 as catalysts for synthesis of coumarin under solvent-free conditions
Nasseri, Mohammad Ali,Sadeghzadeh, Seyed Mohsen
, p. 27 - 33 (2014/01/23)
Fe3O4-diazabicyclo[2.2.2]octane (Fe3O 4-DABCO) magnetic nanoparticles (MNPs) catalyst was readily prepared from inexpensive starting materials in aqueous media which catalyzed the synthesis of coumarin. FTIR spectroscopy, X-ray diffraction, transmission electron micrographs were employed to characterize the properties of the synthesized Fe3O4-DABCO MNPs. High catalytic activity and ease of recovery from the reaction mixture using external magnet, and several reuse times without significant losses in performance are additional eco-friendly attributes of this catalytic system.
CuFe2O4 nanoparticles: A magnetically recoverable and reusable catalyst for the synthesis of coumarins via pechmann reaction in water
Baghbanian, Seyed Meysam,Farhang, Maryam
, p. 697 - 706 (2014/01/17)
The synthesis of coumarins by hydroxyalkylation of phenols with ethyl acetoacetate (via Pechmann reaction) is attempted using magnetically separable and reusable CuFe2O4 nanoparticles in water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright
Polyvinylpolypyrrolidone-bound boron trifluoride (PVPP-BF3); A mild and efficient catalyst for synthesis of 4-metyl coumarins via the Pechmann reaction
Mokhtary, Masoud,Najafizadeh, Faranak
experimental part, p. 530 - 532 (2012/08/08)
Polyvinylpolypyrrolidone-supported boron trifluoride has been studied for synthesis of 4-methyl coumarin by the Pechmann reaction. The reaction proceeded smoothly with hydroxyl phenols and ethyl acetoacetate in good yields in ethanol at reflux conditions. The polyvinylpolypyrrolidone-boron trifluoride complex is a non-corrosive and stable solid catalyst elevated Lewis acid property.
Pentafluorophenylammonium triflate (PFPAT): An efficient, metal-free and reusable catalyst for the von Pechmann reaction
Montazeri, Naser,Khaksar, Samad,Nazari, Akbar,Alavi, Seyedeh Soghra,Vahdat, Seyed Mohammad,Tajbakhsh, Mahmood
experimental part, p. 450 - 452 (2011/08/03)
Pentafluorophenylammonium triflate (PFPAT) is used as an efficient catalyst in the von Pechmann condensation of phenols with β-ketoesters leading to the formation of coumarin derivatives. Short reaction times, easy and quick isolation of the products, excellent chemoselectivity, excellent yields and ease of catalyst recovery with consistent activity makes this protocol efficient and environmentally benign.
