Three-component condensation of Meldrum’s acid with 2-naphthylamine and esters derived from vanillin

Three-component condensation of Meldrum’s acid (2,2-dimethyl-1,3-dioxane-4,6-dione) with 2-naphthylamine and esters derived from vanillin involves intermediate formation of N-arylmethylidene-2-naphthylamines which are cleaved with Meldrum’s acid to give 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones and arylmethylideneketenes. Reaction of the latter with 2-naphthylamine leads to formation of 2-methoxy-4-(3-oxo-1,2,3,4-tetrahydrobenzo[f]quinolin-1-yl)phenyl carboxylates.     

Asymmetric Cu-catalyzed 1,6-conjugate addition of dialkylzinc reagents to 5-(3-aryl-2-propenylidene) Meldrum’s acids

The asymmetric synthesis of tertiary and quaternary stereocentres has been successfully achieved through Cu-catalyzed 1,6-addition of dialkylzinc reagents to 5-(3-aryl-2-propenylidene) Meldrum’s acid derivatives in the presence of a phosphoramidite ligand.     

An efficient regioselective sonochemical synthesis of novel 4-aryl-3-methyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridin-6(7H)-ones

An efficient ultrasound-assisted preparation of a series of novel 4-aryl-3-methyl-4,5-dihydro-l//-pyrazolo[34-b]pyridin-6(7H)ones via the reaction of 5-amino-3-methyl-1H-pyrazole,Meldrum’s acid and various arylaldehydes using one-pot three-component approach is described.This rapid method produced the products in short reaction times(3-4 min) and excellent yields(87-95%).     

Acyl/aroyl Meldrum’s acid as an enol surrogate for the direct organocatalytic synthesis of α,β-unsaturated ketones

The operationally simple, robust and straightforward organocatalytic protocol is developed for the synthesis of E-selective α,β-unsaturated ketones. The method utilizes simple and easily accessible starting materials such as Meldrum’s acid, carboxylic acid, aldehyde and simple bifunctional amine catalyst. The tandem organocatalytic process utilizes acyl/aroyl Meldrum’s acid as an enol surrogate for the effective Doebner-Knoevenagel type condensation reactions. A wide variety of aldehydes, carboxylic acids and base sensitive functional groups are well tolerated under the mild reaction conditions.     

A combination of green solvent and ultrasonic irradiation promotes the catalyst-free reaction of aldehydes,indoles and Meldrum’s acid

Research on Chemical Intermediates - A facile and practical approach for the preparation of 3-indole derivatives was performed by the Yonemitsu condensation of indoles with Meldrum’s acid and...     

Synthesis of Bis‐spiro Cyclopropanes Based on Meldrum’s Acid by Milling

Reaction of 2,2‐dimethyl‐1,3‐dioxane‐4,6‐dione (Meldrum’s acid) with various solid aldehydes in the presence of cyanogen bromide and solid sodium ethoxide (EtONa) leads to the selective and efficient formation of bis‐spiro cyclopropanes based on Meldrum’s acid at the range of 0 °C to room temperature. The products were obtained in good to excellent yields. Structure elucidation is carried out by ¹H NMR, ¹³C NMR, FT‐IR spectroscopy, mass analyses and X‐ray crystallography techniques. A possible mechanism for the formation of products is also discussed under solvent‐free condition.     

4-羟基香豆素及其衍生物的简便合成及其荧光性质的研究

用米氏酸和苯酚在无溶剂条件下以90.6%的收率合成丙二酸单苯基酯, 然后用Eaton试剂(五氧化二磷＋甲基磺酸)在温和条件下闭环, 以78.8%的收率得到4-羟基香豆素, 将这种方法扩展合成了苯环上带有各种取代基的4-羟基香豆素衍生物以及4-羟基硫代香豆素衍生物. 并对部分4-羟基香豆素衍生物的荧光性质进行了研究.     

Facile one-pot synthesis,butyrylcholinesterase and α-glucosidase inhibitory activities,structure–activity relationship,molecular docking and DNA–drug binding analysis of Meldrum’s acid derivatives

Research on Chemical Intermediates - Meldrum’s acid derivatives were facile synthesized by one-pot condensation process and characterized by NMR (1H, 13C, DEPT-90 and DEPT-135) and EI-MS. The...     

Alkyl 3-nitroacrylates: Synthesis and reactions with cyclohexane-1,3-diones and Meldrum’s acid

A modified procedure was proposed for the synthesis of alkyl 3-nitroacrylates by nitroiodination of alkyl acrylates and subsequent dehydroiodination of iodonitropropanoates with triethylamine. Alkyl 3-nitroacrylates reacted with cyclohexane-1,3-dione, dimedone, and Meldrum’s acid in the presence of N,N,N-tri-methylanilinium hydroxide (Rodionov’s catalyst) in anhydrous methanol to give the corresponding Michael adducts.     

Synthesis of spiro-fused heterocycles under aerobic conditions by using polymer gel-entrapped catalyst

Research on Chemical Intermediates - An expedient synthesis of spiro-fused heterocycles from multi-component reaction of urea, aryl aldehydes and Meldrum’s or barbituric acid by using polymer...     

Three-component condensation of 3-aminothiophene derivatives with isatines and Meldrum’s acid. Synthesis of 2,5′-dioxo-3′-phenyl-5′,6′-dihydro-4′H-spiro[indoline-3,7′-thieno[3,2-b]pyridine]-2′-carboxylic acids

A method for the synthesis of 2,5′-dioxo-3′-phenyl-5′,6′-dihydro-4′H-spiro[indoline-3,7′-thieno[3,2-b]pyridine]-2′-carboxylic acids was elaborated based on the three-component condensation of 3-aminothiophenes, Meldrum’s acid, and isatines.     

Survey reactivity of 2-aminopyridine and Meldrum’s acid in the presence of aryl glyoxals or aryl aldehydes; ethyl 2-(3-aryl imidazo[1,2-a]pyridin-2-yl)acetates versus ethyl 3-aryl-3-(pyridin-2-ylamino)propanoates

Research on Chemical Intermediates - The aim of present investigation is survey reactivity of 2-aminopyridine and Meldrum’s acid in the presence of aryl glyoxals or aryl aldehydes. The ethyl...     

Multi-component condensation of 4-hydroxy-6-methyl-1H-pyridin-2-one with carbonyl compounds and Meldrum’s acid

A convenient method for the synthesis of earlier unknown substituted derivatives of 4-aryl-7-methyl-4,6-dihydro-3H-pyrano[3,2-c]pyridine-2,5-dione and ethyl 3-(4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)-3-arylpropionate was developed based on the multi-component condensation of 4-hydroxy-6-methyl-1H-pyridin-2-one, Meldrum’s acid, and carbonyl compounds.     

One-pot synthesis of benzoquinoline and coumarin derivatives using Meldrum’s acid in three-component reactions

A series of 1-aryl-1,2-dihydrobenzo[f]quinolin-3(4H)-one derivatives and 4-aryl-7,7-dimethyl-5-oxo-3,4,5,6,7,8-hexahydrocoumarin derivatives have been synthesized by one-pot multicomponent reaction of Meldrum’s acid with benzaldehyde, naphthalene-2-amine, or cyclohexanedione in PEG-400. The method has the advantages of mild reaction conditions, good yields, and easy processing, and is environmentally benign.     

One-pot three-component green synthesis of novel dihydrophthalazine-1,4-diones

Green and efficient one-pot three-component synthesis of novel 2-(7-amino-2,2-dimethyl-4-oxo-5-phenyl-4,5-dihydropyrano[2,3-d][1,3]dioxin-6-ylcarbonyl)-2,3-dihydrophthalazine-1,4-diones have been developed by condensing 3-(1,4-dioxo-1,2,3,4-tetrahydrophthalazin-2-yl)-3-oxopropanenitrile with benzaldehydes and Meldrum’s acid using L-proline as catalyst in ethanol at room temperature. The products have been isolated as pure compounds in good yields without using column chromatography.     

Catalyst-free synthesis of 1,2,4,5-tetrasubstituted imidazoles from arylamins,benzonitriles, arylglyoxals,and Meldrum’s acid

An efficient and catalyst-free for the synthesis of 1,2,4,5-tetrasubstituted imidazoles has been developed using a one-pot, two-step reaction of arylamins, benzonitriles, arylglyoxals, and Meldrum’s acid. All the products were obtained in good to excellent yields and their structures were established from their spectroscopic data.     

A short synthesis of 3-enoyltetramic acids employing a new acyl ylide conjugate of Meldrum’s acid

2,2-Dimethyl-5-(triphenylphosphoranylidene)acetyl-1,3-dioxan-4,6-dione (3) is a new activated β-ketoacyl equivalent, readily prepared in quantitative yield by reaction of Meldrum’s acid with the stable ylide Ph₃PCCO. Its reaction with α-amino esters affords the corresponding N-(β-ketoacyl)amino ester ylides which, when treated with aldehydes and KOtBu, undergo a simultaneous Wittig olefination cum Dieckmann cyclisation to yield the respective 3-enoyltetramic acids.     

Co(NO<Subscript>3</Subscript>)<Subscript>2</Subscript>·6H<Subscript>2</Subscript>O as a powerful and reusable catalyst for the synthesis of phenylbenzo[<Emphasis Type="Italic">g</Emphasis>]chromenes

An efficient and easy protocol for the one-pot three-component synthesis of phenylbenzo[g]chromenes was developed. The synthesis was achieved by the reaction of aromatic aldehydes, Meldrum’s acid, and 2-hydroxynaphthalene-1,4-dione in the presence of catalytic amount of Co(NO₃)₂·6H₂O at room temperature. The important advantages of this procedure are short reaction times, high yields, easy work-up, reusable catalyst, and no need to column chromatography.     

An efficient synthesis of new khellactone-type compounds using potassium hydroxide as catalyst via one-pot,three-component reaction

In the present work, three-component synthesis for novel khellactone-type compounds via the reaction of Meldrum’s acid, aryl aldehydes and 5,7-dihydroxy benzopyrone derivatives was described. In this reaction 10-aryl substituted-9,10-dihydropyrano[2,3-h]benzopyrone-8-ones as new khellactone analogous in the presence of catalytic amount of potassium hydroxide as cheap and green basic catalyst were obtained in good to excellent yields under refluxing methanol.     

Diastereoselective trimolecular condensation between indole,Meldrum’s acid and chiral sugar-derived aldehydes

The trimolecular condensation of indole, Meldrum’s acid and chiral, sugar-derived aldehydes took place in good yield and high diastereoselectivity. The absolute configuration of the α-carbon of the chiral aldehydes ensured a predictable diastereocontrol of the newly created stereogenic centre except for (3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[3,2-d][1,3]dioxole-5-carbaldehyde 3i. In this case, the opposite stereochemistry may be explained by a less congested conformer of the Knoevenagel-adduct intermediate.