Natural phosphate-supported Cu( ii ), an efficient and recyclable catalyst for the synthesis of xanthene and 1,4-disubstituted-1,2,3-triazole derivatives

作者: Abbas Amini , Azadeh Fallah , Chun Cheng , Mahmood Tajbakhsh

DOI: 10.1039/C8RA08260J

关键词:

摘要: Cu(NO3)2 supported on natural phosphate, Cu(II)/NP, was prepared by co-precipitation and applied as a heterogeneous catalyst for synthesizing xanthenes (2–3 h, 85–97%) through Knoevenagel–Michael cascade reaction of aromatic aldehydes with 1,3-cyclic diketones in ethanol under refluxing conditions. It further used regioselective synthesis 1,4-disubstituted-1,2,3-triazoles (1–25 min, 95–99%) via three-component between organic halides, alkynes sodium azide methanol at room temperature. The proposed catalyst, characterized using X-ray fluorescence, diffraction, Fourier-transform infrared spectroscopy, scanning electron microscopy, Brunauer–Emmett–Teller, Barrett–Joyner–Halenda inductively coupled plasma analyses. Compared to other reports literature, the reactions took place simple co-precipitation, having short time ( 85%), high recyclability (>5 times) without significant decrease inherent property selectivity catalyst. protocols provided economic environmental advantages.

参考文章(101)
Tomohiro Yasukawa, Aya Suzuki, Hiroyuki Miyamura, Kohei Nishino, Shu̅ Kobayashi, Chiral Metal Nanoparticle Systems as Heterogeneous Catalysts beyond Homogeneous Metal Complex Catalysts for Asymmetric Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds. Journal of the American Chemical Society. ,vol. 137, pp. 6616- 6623 ,(2015) , 10.1021/JACS.5B02213
Mahshid Rahimifard, Ghodsi Mohammadi Ziarani, Alireza Badiei, Shima Asadi, Ali Abolhasani Soorki, One-pot solvent-free synthesis of 1,8-dioxo-octahydroxanthene derivatives using sulfonic acid-functionalized LUS-1 and their antimicrobial activities Research on Chemical Intermediates. ,vol. 42, pp. 3847- 3861 ,(2016) , 10.1007/S11164-015-2248-2
A. Małecki, R. Gajerski, S. Łabuś, B. Prochowska-Klisch, K. T. Wojciechowski, Mechanism of Thermal Decomposition of d-metals Nitrates Hydrates Journal of Thermal Analysis and Calorimetry. ,vol. 60, pp. 17- 23 ,(2000) , 10.1023/A:1010155931266
A. Sarkar, T. Mukherjee, S. Kapoor, PVP-Stabilized Copper Nanoparticles: A Reusable Catalyst for “Click” Reaction between Terminal Alkynes and Azides in Nonaqueous Solvents Journal of Physical Chemistry C. ,vol. 112, pp. 3334- 3340 ,(2008) , 10.1021/JP077603I
Khodabakhsh Niknam, Farhad Panahi, Dariush Saberi, Molki Mohagheghnejad, Silica‐bonded S‐sulfonic acid as recyclable catalyst for the synthesis of 1,8‐dioxo‐decahydroacridines and 1,8‐dioxo‐octahydroxanthenes Journal of Heterocyclic Chemistry. ,vol. 47, pp. 292- 300 ,(2010) , 10.1002/JHET.303
Christian W. Tornøe, Caspar Christensen, Morten Meldal, Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. Journal of Organic Chemistry. ,vol. 67, pp. 3057- 3064 ,(2002) , 10.1021/JO011148J
Alessia CORAMI, Silvano MIGNARDI, Vincenzo FERRINI, Removal of Lead, Copper, Zinc and Cadmium from Water Using Phosphate Rock Acta Geologica Sinica-english Edition. ,vol. 82, pp. 1223- 1228 ,(2010) , 10.1111/J.1755-6724.2008.TB00724.X