Ultrasound-assisted one-pot, three-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones

Triethylamine was found to be an efficient catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones by one-pot reaction of phthalhydrazide, aromatic aldehydes, and malononitrile or ethyl cyanoacetate in ethanol under ultrasonic irradiation. The advantages of this method are the use of an inexpensive and readily available catalyst, easy workup, improved yields, and the use of ethanol as a solvent that is considered to be relatively environmentally benign.     

Knoevenagel reaction in water catalyzed by amine supported on silica gel

Summary An environmentally benign and sustainable Knoevenagel reaction of aldehyde with ethyl cyanoacetate has been achieved at ambient temperature in water employing 3-aminopropylated silica gel (NAP) as a catalyst. Wide applicability of the reaction is illustrated by the results that not only arylaldehydes of both electronic characters but also aliphatic aldehydes afforded the products. The reaction condition was so mild that aldehydes having acid- or base-sensitive substituents provided substituted α-cyano-α, β-unsaturated esters. The catalyst has been efficiently recycled more than five times without any pre-treatment. Catalyst loading was successfully reduced to 0.0029 mmol% (TON = up to 9,226). This protocol was also applicable to the Knoevenagel reaction of malononitrile in good yields in water.     

Diammonium hydrogen phosphate as a versatile and efficient catalyst for the one-pot synthesis of pyrano[2,3-<Emphasis Type="Italic">d</Emphasis>]pyrimidinone derivatives in aqueous media

Diammonium hydrogen phosphate, (NH(4))(2)HPO(4), was used as a catalyst for one-pot, three-component condensation reactions consisting of aromatic aldehydes, malononitrile and barbituric/thiobarbituric acid in aqueous ethanol at room temperature. This method has the advantages of a simple operation, mild reaction conditions, high yields, by using a less toxic and low cost chemical as a catalyst.     

New multicomponent approach for the synthesis of benzo[c]coumarin derivatives over MgO under solvent-free conditions

In this study, a three-component one-pot synthesis of select 5-amino-6-cyano-3-hydroxybenzo[c]coumarin compounds derived from salicylaldehydes, malononitrile, and ethyl acetoacetate is reported. The reaction is conducted on grinding over MgO at room temperature resulting in good yields.     

An efficient three-component, one-pot synthesis of 2-alkylthio-4-amino-5-cyano-6-aryl(alkyl)pyrimidines in water

A convenient and practical method for the synthesis of 2-alkylthio-4-amino-5-cyano-6-aryl(alkyl)pyrimidines has been developed via a three-component, one-pot reaction from aldehydes, malononitrile and S-alkylisothiouronium salts in water at room temperature. A series of polysubstituted pyrimidines were prepared by this method in moderate to excellent yields. In addition, two kinds of pyrimidine-fused heterocyclic derivatives with potential pharmacological activity were constructed from our 2-alkylthio-4-amino-5-cyano-6-arylpyrimidines.     

Ultrasound mediated,iodine catalyzed green synthesis of novel 2-amino-3-cyano-4H-pyran derivatives

An efficient synthesis of a novel series of twelve substituted 2-amino-3-cyano-4H-pyran derivatives was achieved by a one-pot three-component cyclocondensation reaction of heteroaryl aldehydes, malononitrile and active methylene compounds catalyzed by iodine in aqueous medium under ultrasound irradiation. In comparison with conventional methods, our protocol is convenient and offers several advantages, such as shorter reaction time, higher yields, milder conditions and environmental friendliness. We have herein successfully demonstrated the synergistic outcome of multi-component reaction (MCR) and sonication to offer a facile route for the design of these derivatives.     

A one-pot microwave-assisted synthesis of pyrido[2,3-d]pyrimidines

A high yield multicomponent reaction providing multifunctionalized pyrido[2,3-d]pyrimidines with up to four diversity centers in a one-pot microwave-assisted cyclocondensation of alpha,beta-unsaturated esters, amidine systems and malononitrile (or ethyl cyanoacetate) is described.     

Ultrasound promoted one-pot synthesis of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile scaffolds in aqueous media: A complementary ‘green chemistry’ tool to organic synthesis

A green and simple approach to assembling of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile scaffolds via three-component reaction of kojic acid, malononitrile, and aromatic aldehydes in aqueous media under ultrasound irradiation is described. The combinatorial synthesis was achieved for this methodology with applying ultrasound irradiation while making use of water as green solvent. In comparison to conventional methods, experimental simplicity, good functional group tolerance, excellent yields, short routine, and selectivity without the need for a transition metal or base catalyst are prominent features of this green procedure.     

Ultrasound-promoted an efficient method for one-pot synthesis of 2-amino-4,6-diphenylnicotinonitriles in water: a rapid procedure without catalyst

A green and convenient approach to the synthesis of 2-amino-4,6-diphenylnicotinonitriles via four-component reaction of malononitrile, aromatic aldehydes, acetophenone derivatives and ammonium acetate in water under ultrasound irradiation is described. The combinatorial synthesis was achieved for this methodology with applying ultrasound irradiation while making use of water as green solvent. In comparison to conventional methods, experimental simplicity, good functional group tolerance, excellent yields, short routine, and selectivity without the need for a transition metal or base catalyst are prominent features of this sonocatalyzed procedure.     

Glycine catalyzed convenient synthesis of 2-amino-4H-chromenes in aqueous medium under sonic condition

A one-pot three-component condensation of an aldehyde, malononitrile, and resorcinol has been achieved by ultrasound method. The reaction has been catalyzed by glycine in aqueous medium. This protocol afforded corresponding 2-amino-4H-chromenes in shorter reaction times, high yields and simple work-up procedures with the green aspects by avoiding toxic reagents.     

Ionic liquid promoted preparation of 4H-thiopyran and pyrimidine nucleoside-thiopyran hybrids through one-pot multi-component reaction of thioamide

One-pot multi-component reactions of aldehydes, cyanothioacetamide and malononitrile promoted by ionic liquid proved to be an efficient way for the synthesis of thiopyran derivatives. Without any added catalyst, both aromatic and aliphatic aldehydes participated in this reaction smoothly. As an application of this method, a pyrimidine nucleoside-thiopyran chimera with potential biological activities was obtained in high yield from 5-formyl-2’-deoxyuridine. In addition, the ionic liquid used can be easily recovered and effectively reused for at least 5 times. Electronic supplementary material  The online version of this article (doi:) contains supplementary material, which is available to authorized users.     

A novel and environment-friendly method for preparing dihydropyrano[2,3-c]pyrazoles in water under ultrasound irradiation

A green and convenient approach to the synthesis of dihydropyrano[2,3-c]pyrazoles via four-component reaction of aromatic aldehydes, hydrazine, ethyl acetoacetate and malononitrile in water under ultrasound irradiation is described. This method provides several advantages such as environmental friendliness, shorter reaction time, excellent yields, and simple workup procedure.     

Synthesis of ethyl α-cyanocinnamates under ultrasound irradiation

Knoevenagel condensation of ethyl cyanoacetate with aromatic aldehydes catalyzed by pyridine results ethyl α-cyanocinnamates in 80–96% yields under ultrasound irradiation.     

Regioselective synthesis of pyrimidine-fused tetrahydropyridines and pyridines by microwave-assisted one-pot reaction

Molecular Diversity - A regioselective three-component reaction of α,β-unsaturated aldehydes, cyclic 1,3-dicarbonyls and 6-aminouracils in the presence of FeCl3·6H2O as catalyst...     

A green one-pot three-component cascade reaction: the synthesis of 2-amino-5,8-dihydro-3H-pyrido[2,3-D]pyrimidin-4-ones in aqueous medium

A one-pot three-component cascade reaction for the green synthesis of a new class of 2-amino-5,8-dihydro-3H-pyrido[2,3-d]pyrimidin-4-ones was developed from the condensation of aromatic aldehydes with 2,6-diaminopyrimidin-4(3H)-one and acetophenone derivatives or various cyclic ketones in the presence of a catalytic amount of sodium carbonate in a mixture of water and ethanol at 60  \({^{\circ }}\hbox {C}\). This reaction led to the construction of two carbon–carbon bonds and one carbon–nitrogen bond in a single synthetic step.     

A novel four- and pseudo-five-component reaction: unexpected efficient one-pot synthesis of 4<Emphasis Type="Italic">H</Emphasis>-thiopyran derivatives

A facile and convenient novel method is reported for the synthesis of substituted 4H-thiopyrans by reacting aldehydes, malononitrile, carbon disulfide, and primary amines at room temperature in the presence of triethylamine as a catalyst. This reaction affords the desired products in high purity and has advantages of excellent yields, simple work-up procedure, and short reaction time.     

A new one-pot three-component synthesis of 2,4-diamino-5<Emphasis Type="Italic">H</Emphasis>-chromeno[2,3-<Emphasis Type="Italic">b</Emphasis>]pyridine-3-carbonitrile derivatives

In this study, a three-component one-pot synthesis of new 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles derived from 2-amino-1,1,3-tricyanopropene, salicylic aldehydes and secondary cyclic amines is reported. The reaction is conducted in ethanol at ambient temperature in good-to-excellent yields.     

CaCl2 as a bifunctional reusable catalyst: diversity-oriented synthesis of 4H-pyran library under ultrasonic irradiation

CaCl₂ is applied as an efficient reusable and eco-friendly bifunctional catalyst for the one-pot three-component synthesis of 4H-pyrans under ultrasonic irradiation. A broad range of substrates including the aromatic and heteroaromatic aldehydes, indoline-2,3-dione (isatin) derivatives, acenaphthylene-1,2-dione (acenaphthenequinone) and 2, 2-dihydroxy-2H-indene-1,3-dione (ninhydrin) were condensed with carbonyl compounds possessing a reactive ??-methylene group and alkylmalonates. All reactions are completed in short times, and the products are obtained in good to excellent yields. The catalyst could be recycled and reused several times without any loss of efficiency.     

Ultrasound-assisted three-component synthesis of 3-(5-amino-1H-pyrazol-4-yl)-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)indolin-2-ones in water

Indium(III) chloride was found to be an efficient catalyst for the synthesis of 3-(5-amino-1H-pyrazol-4-yl)-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)indolin-2-ones by one-pot, three-component reaction of dimedone, 1H-pyrazol-5-amines and isatins in water under ultrasonic irradiation. The advantages of this method are the use of a readily available catalyst, easy workup, excellent yields, and the use of water as a solvent that is considered to be relatively environmentally benign.     

Ultrasound promoted ZrCl(4) catalyzed rapid synthesis of substituted 1,2,3,4-tetrahydropyrimidine-2-ones in solvent or dry media

Sonication of aromatic aldehydes, urea and ethyl acetoacetate in presence of solvent (ethyl alcohol) or solvent-less dry media (bentonite clay) supported-zirconium (IV) chloride (ZrCl(4)) as catalyst at 35 kHz gives 6-methyl-4-substitutedphenyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl esters proficiently in high yields.