Facile and efficient synthesis of 3,4,5-substituted furan-2(5H)-ones by using β-cyclodextrin as reusable catalyst

3,4,5-Substituted furan-2(5H)-one derivatives were synthesized by using β-cyclodextrin as a catalyst in water via biomimetic approach. β-Cyclodextrin can be recovered and reused.     

An efficient one-pot multi-component synthesis of 3,4,5-substituted furan-2(5H)-ones catalyzed by tetra-n-butylammonium bisulfate

A facile one-pot synthesis of 3,4,5-substituted furan-2(5H)-one derivatives from a three-component reaction of aniline derivatives, dialkylacetylenedicarboxylates and aromatic aldehydes under mild conditions using tetra-n-butylammonium bisulfate as a catalyst has been developed.     

ZnO nanoparticle-catalyzed efficient one-pot three-component synthesis of 3,4,5-trisubstituted furan-2(5H)-ones

An efficient and high-yielding protocol using nano-ZnO (50–100 nm) as an efficient heterogeneous catalyst for one-pot three-component synthesis of pharmacologically significant furanone derivatives by the condensation of aromatic aldehyde, amine and dimethylacetylenedicarboxylate has been developed. Since the catalyst is heterogeneous, it can be easily separated and recycled several times without much loss of its catalytic activity. Use of aqueous medium, recyclable nanocatalyst, operational simplicity, non-chromatographic purification technique, excellent yield and short reaction time makes this approach an attractive protocol for the synthesis of 3,4,5-trisubstituted furan-2(5H)-ones.     

Vitamin B12:An efficient type catalyst for the one-pot synthesis of 3,4,5-trisubstituted furan-2(5H)-ones and N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates

Vitamin B12 was applied as catalyst for the one-pot three-component synthesis of 3,4,5-trisubstituted furan-2(5H)-ones from the condensation between aldehydes, amines and dialkylacetylendicarboxylates at ambient temperature in EtOH. In addition, N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates were synthesised using mentioned catalyst at ambient temperature in EtOH from condensation between formaldehyde, amines, and dialkylacetylenedicarboxylates. This methodology has number of advantages such as:use of green and nonhazardous catalyst, clean work up, short reaction times, high yields and no need to column chromatography.     

Azo coupling of 5-substituted furan-2(3H)-ones and 1H-pyrrol-2(3H)-ones with arene(hetarene)diazonium salts

5-Substituted furan-2(3H)-ones and 1-phenyl-1H-pyrrol-2(3H)-ones reacted with diazonium salts derived from substituted anilines and 1H-1,2,4-triazol-5-amine to give azo coupling products at the methylene group in the heteroring. The products were found to exist as hydrazone tautomers.     

Synthesis of 3,4,5-substituted furan-2(5<Emphasis Type="Italic">H</Emphasis>)-ones using Al-doped ZnO nanostructure

Al-doped ZnO nanostructures were prepared via a simple precipitation method and were characterized by several techniques including XRD, TEM, EDX, UV–Vis, and DLS. All XRD patterns show the hexagonal single-phase structure of pure and Al-doped ZnO nanopowders without impurity. The samples consist of particles with average sizes ranging from 53 to 60 nm measured by DLS technique. Next, the catalytic activity of pure and Al-doped ZnO nanopowders was investigated in terms of synthesis of 3,4,5-substituted furan-2(5H)-one derivatives using the three-component reaction of aldehydes, aromatic amines, and acetylenic esters. This procedure has advantages such as high yields, simple methodology, and easy work-up.     

Cyclocondensation of 3-acetylfuran-2(5H)-ones with benzylidenemalononitrile. Synthesis of 3-(5-amino-4,6-dicyanobiphenyl-3-yl)furan-2(5H)-ones

Russian Journal of Organic Chemistry -     

Efficient One-Pot Synthesis of Alkyl 2-(Bromomethyl)-2-(4-aryl)-4-alkoxy-5-oxo-2,5-dihydrofuran-3-carboxylate

One-pot, three-component reaction of different phenacyl bromides and dialkylacetylenedicarboxilates was carried out with triphenylphosphine and functionalized oxodihydrofuran derivatives in excellent yields.     

Synthesis of 4-acyl(alkoxycarbonyl)-5-fluoroalkyl-3,5-dihydroxyfuran-2(5H)-ones

4-Acyl(alkoxycarbonyl)-5-fluoroalkyl-3,5-dihydroxyfuran-2(5H)-ones were obtained for the first time by the reactions of fluoroalkyl-containing 1,3-diketones and 3-oxo esters with oxalyl chloride.     

Reaction of furan-2(3H)-ones with 1,2-binucleophiles

Reactions of 5-substituted furan-2(3H)-ones with ethylenediamine, 2-aminoethanol, and o-aminophenol do not stop at the stage of formation of the corresponding 4-oxoalkanoic acid amides but lead to new bi-and tricyclic structures as a result of double intramolecular cyclodehydration.     

Highly efficient solvent-free synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones using tetrabutylammonium bromide as novel ionic liquid catalyst

<正>A simple and efficient procedure for the synthesis of 2-arylquinazolin-4(3H)-ones has been developed through cyclocondensation of 2-aminobenzamide with aromatic aldehydes using tetrabutylammonium bromide(TBAB) as novel neutral ionic liquid catalyst in the presence of copper(Ⅱ) chloride(CuCl_2) as oxidizing agent under solvent-free conditions at 100℃.In the absence of CuCl_2 and under a nitrogen atmosphere,the unoxidized intermediates,2-aryl-2,3-dihydroquinazolin-4(1H)-ones,were isolated. Treatment of these intermediates with CuCl_2 in TBAB media gave the oxidized products 2-arylquinazolin-4(3H)-ones.On the other hand,cyclocondensation of 2-aminobenzamide with aromatic aldehydes in TBAB under microwave irradiation directly gave 2- arylquinazolin-4(3H)-ones.     

First asymmetric cycloaddition of carbonyl ylides to vinyl sulfoxides and furan-2(5H)-ones

The Rh2(OAc)4-catalyzed reactions of o-(methoxycarbonyl)-alpha-diazoacetophenone with enantiomerically pure 5-ethoxy-3-p-tolylsulfinylfuran-2(5H)-ones 1a and 1b afford 4,10-epoxybenzo[4,5]cyclohepta[1,2-c]furan-3,9-diones 6a and 6b, in good or moderate yields and in a completely regioselective way. The pi-facial selectivity is complete for 1a, which only yields anti-6a adducts, and very high for 1b. The endo stereoisomers are favored with respect to the exo ones in both reactions. The sulfinyl group significantly increases the reactivity of the dipolarophile as it has been demonstrated by studying the behavior of 5-methoxyfuran-2(5H)-one (3).     

Potassium aluminum sulfate (alum): an efficient catalyst for the one-pot synthesis of trisubstituted imidazoles

Trisubstituted imidazoles were synthesized in high yields in the presence of potassium aluminum sulfate (alum) as a non-toxic, reusable, inexpensive, and easily available reagent at 70°C.     

Potassium aluminum sulfate (alum): an efficient catalyst for the one-pot synthesis of trisubstituted imidazoles

Trisubstituted imidazoles were synthesized in high yields in the presence of potassium aluminum sulfate (alum) as a non-toxic, reusable, inexpensive, and easily available reagent at 70°C. Correspondence: Ali A. Mohammadi, Department of Chemistry, Faculty of Science, Islamic Azad University-branch Sabzevar, P.O. Box 9618814711, Sabzevar, Iran.     

Aluminum hydrogen sulfate [Al(HSO4)3] as an efficient catalyst for the preparation of thioacetals

Aluminum hydrogen sulfate, as a heterogeneous solid acid catalyst, has been used for the mild conversion of carbonyl compounds to their thioacetals using 1,2- and 1,3-dithiol under ambient conditions with short reaction times in high to excellent yield in acetonitrile as solvent.     

Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using aluminum methanesulfonate as a reusable catalyst

A wide range of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones were synthesized via a one-pot three components condensation of isatoic anhydride, aldehydes, and ammonium salts or primary amines in the presence of aluminum methanesulfonate in EtOH/H₂O solution. The catalyst is reusable and could be recycled for several runs without any distinct decrease in its efficiency. A plausible mechanism for this one-pot three components reaction was proposed.     

Addition reactions of thiazol-5(4H)-ones—II : Cycloaddition and Michael addition reactions of 4-substituted 2-phenylthiazol-5(4H)-ones

The mixture of adducts formed under mild conditions between a 4-substituted 2-phenylthiazol-5(4H)-one and an electron-deficient alkene is shown to include a stable cycloadduct and a Michael adduct formed through the 2- or the 4-position of the thiazolone. The reaction can be diverted towards the Michael adduct entirely, by adding traces of aqueous alkali to the reactants in acetone solution. A novel type of 1:2-adduct is present in the reaction mixture, and is shown to be formed through reaction of the cycloadduct with the alkene. A product formed by extrusion of carbonyl sulphide from the cycloadduct is the same as that obtained from the analogous oxazolone and the alkene, but generally the differences between the propensity of oxazolones and thiazolones to undergo various types of addition reaction with representative dipolarophiles are shown to be substantial.