Catalytic Synthesis of Pyrano- and Furoquinolines Using Nano Silica Chromic Acid at Room Temperature (original) (raw)
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Research on Chemical Intermediates, 2013
One-pot four-component synthesis of 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines catalyzed by silicabased sulfonic acid Abstract A series of 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines were synthesized through a rapid one-pot four-component reaction in the presence of heterogeneous silica-based sulfonic acid (SiO 2 -Pr-SO 3 H) under solvent-free conditions.
Journal of Nanostructure in Chemistry
In this work, a library of diverse chemically and medicinally important heterocyclic polyhydroquinoline derivatives was efficiently prepared via a one-pot multicomponent reaction starting from various raw materials including aromatic aldehydes, dimedone or 1,3-cyclohexandione, ethyl acetoacetate or methyl acetoacetate and ammonium acetate in the presence of Fe 3 O 4 /SiO 2-OSO 3 H as a sulfonated silica-based magnetic nanocatalyst in high yields. Main advantages of the present practical approach are ready availability of starting materials, non-toxicity, inexpensiveness, ease of workup procedure, diversity orientation synthesis and an eco-friendly nature of the reaction. The nanocatalyst was characterized by Fourier transform infrared (FT-IR) spectra, scanning electron microscopy (SEM) images and energy-dispersive X-ray spectroscopy (EDX) spectra. The nanocatalyst was simply recovered using an external magnet and reused several times. Then, the pharmacological and biological activities of the products were theoretically examined by the prediction of activity spectra for substances (PASS) program.
IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION
Sulfonic acid functionalized SBA-15 (SBA-Pr-SO 3 H) as a new nanoporous acid catalyst was used in the one-pot synthesis of polyhydroquinolines derivatives via the Hantzsch four component condensation reaction of aldehydes, β -ketoesters, dimedone and ammonium acetate under solvent free conditions with short reaction time in excellent yields. SBA-Pr-SO 3 H was proved to be an efficient heterogeneous nanoporous solid acid catalyst (pore size 6 nm), which could be easily handled and removed from the reaction mixture by simple filtration, and also recovered and reused without loss of reactivity. KEY WORDS: Nanoporous solid acid catalyst, Sulfonic acid functionalized SBA-15, Polyhydroquinolines, Solvent free conditions, Dimedone.
Silica nanoparticles efficiently catalyzed synthesis of quinolines and quinoxalines
Catalysis Science & Technology, 2011
In this work, highly efficient, green and inexpensive procedures for the preparation of quinoxaline and quinoline derivatives as attractive aza-polycyclic compounds are described. Silica nanoparticles-catalyzed condensation of 1,2-diamines with 1,2-diketones under solvent-free conditions at room temperature affords high yields of quinoxalines with short reaction times. Moreover, the microwave-assisted Friedla¨nder hetero-annulation reaction between 2-aminoaryl ketones and carbonyl compounds in the presence of silica nanoparticles (NPs) as catalysts gives high yields of quinoline derivatives with short reaction times. These reactions have been done in neutral conditions. The NPs catalysts can be reused without lost of activity even after recycling fourteen times .
Chinese Journal of Chemistry, 2011
2,3-Dihydroquinazolin-4(1H)-one derivatives were synthesized via a one-pot, three component reaction of isatoic anhydride and an aromatic aldehyde with ammonium acetate or primary amine catalyzed by silica-bonded S-sulfonic acid in ethanol at 80 ℃. The reaction work-up is simple and the catalyst is easily separated from the products by filtration. The heterogeneous catalyst was recycled for ten runs upon the condensation reaction of isatoic anhydride and 4-chlorobenzaldehyde with ammonium acetate without losing its catalytic activity.
Tetrahedron Letters, 2011
A one-pot practical, efficient, and environmentally benign multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications has been developed using a very mild, neutral, and reusable silica nanoparticles as catalyst. The 4H-pyran derivatives were synthesized by a three component reaction of an aldehyde, malononitrile, and 5,5-dimethyl-1,3-cyclohexanedione or ethyl acetoacetate at room temperature or refluxing in
Proceedings of The 18th International Electronic Conference on Synthetic Organic Chemistry, 2014
The classical Hantzsch reaction is one of the simplest and most economical methods for the synthesis of biologically important and pharmacologically useful 1,4-dihydropyridine derivatives. Silica-supported alginic acid-L-glutamic acid (SiO2-AA-L-Glu) under thermal and solvent free conditions is proven to act as a highly efficient catalyst for a one-pot four component reaction of various aldehydes, ammonium acetate, cyclic 1,3-dicarbonyl compounds and ethyl acetoacetate for the synthesis of biologically active substituted Hantzsch 1,8dioxohexahydroacridine and polyhydroquinoline derivatives in excellent yields. The present environmentally benign procedure for the synthesis of 1,4-dihydropyridines is suitable for library synthesis and it will find application in the synthesis of potent biologically active molecules. The process presented here is operationally simple, environmentally benign and has excellent yield with short reaction time and straightforward workup. Furthermore, the catalyst can be recovered conveniently and reused efficiently.
Molecular Catalysis, 2018
This paper presents investigation on the synthesis of 2,2,4-trimethyl-1,2-H-dihydroquinoline (TMQ) as a result of the reaction of aniline and both acetone and mesityl oxide in the presence of selected sulfonic acid silica catalysts. Condensation of aniline with acetone is very complex process with the formation of significant number of side products, both desirable and undesirable considering the final product (TMQ). In acidic conditions and elevated reaction temperature the reactivity of main raw materials (aniline, acetone) is significantly high, what causes the formation of many side by-products lowering the selectivity of this reaction. In this paper the reaction of aniline with acetone in the presence of heterogeneous acidic silica catalysts were investigated in more detail and discussed. The results were confirmed by GC/MS analysis, that the presence of TMQ isomers and other byproducts significantly affected the formation of final product. The formation of previously not described structural isomer of TMQ has been also demonstrated.