Three-component Reaction Of Isatins Research Articles

A Simple and Efficient Procedure for the One-pot Three-component Synthesis of Spiro[indoline-3,9′-tetrazolo[5,1-b]quinazoline]-2,8′(5′H)-dione in PEG–H2O Medium

Abstract Novel spiro[indoline-3,9′-tetrazolo[5,1-b]quinazoline]-2,8′(5′H)-dione derivatives have been synthesized by the three-component reaction of isatin, 5-amino-1H-tetrazole, and 5,5-dimethylcyclohexane-1,3-dione in PEG–H2O medium catalyzed by p-TSA. This protocol provides a simple one-step procedure with the advantages of easy work-up, mild reaction conditions, and environmental benignity.

Indium Trichloride Catalysed Domino Reactions of Isatin: A Facile Access to the Synthesis of Spiro(indoline-3,4′-pyrano[2,3-c]pyrazol)-2-one Derivatives

A versatile high-yielding indium trichloride mediated one-pot regioselective synthesis of spiroxindoles via domino one-pot, three-component reaction of isatins, pyrazoles, and (<i>E</i>-)-<i>N</i>-methyl-1-(methylthio)-2-nitroethenamine is described. This reaction presumably occurs via domino Knoevenagel condensation–­Michael addition–intramolecular O-cyclization sequence. The salient features of the methodology are its clean reaction conditions, the eco-friendly medium, low cost, easy isolation, and excellent yields without column chromatographic purification.

Greener synthesis of spirooxindole in deep eutectic solvent

A simple and efficient synthesis of spirooxindole derivatives by one-pot, three-component reaction of isatins, malononitrile and different nucleophiles under catalyst-free condition in deep eutectic solvent is reported. A series of biological importance, spirooxindole derivatives were synthesized via a multicomponent reaction of isatin, or acenaphthoquinone, and malononitrile or cyanoacetic ester with 1,3-dicarbonyl compounds, naphtol and 4-hydroxycumarin in biodegradable choline chloride based deep eutectic solvent in good yields (50–95%). This green procedure has the advantages of higher yields, shorter reaction times, environmental friendliness, and easy work-up.

A simple and clean method for multicomponent synthesis of spiro [indole-tetrahydropyrano(2,3-d)pyrimidine] derivatives using SBA-Pr-SO3H as catalyst under solvent-free conditions

Sulfonic acid functionalized SBA-15 (SBA-Pr-SO3H) as a new nanoporous solid acid catalyst was applied in the green one-pot synthesis of spiro[indole-tetrahydropyrano(2,3-d)pyrimidine] derivatives via three-component reaction of isatins, malononitrile or cyanoacetic esters and barbituric acids under solvent-free conditions. SBA-Pr-SO3H was proved to be an efficient heterogeneous nanoporous solid acid catalyst with a pore size of 6 nm, which could be easily handled and removed from the reaction mixture by simple filtration and can be recovered and reused several times without any loss of activity. The advantages of this methodology are high product yields, being environmentally benign, short reaction times, and easy handling.

Synthesis of novel spirooxindoles in water by using MnFe2O4 nanoparticles as an efficient magnetically recoverable and reusable catalyst

An efficient, clean, atom-economical and simple method for the one-pot synthesis of novel spirooxindole derivatives via a three-component reaction of isatins, dimedone and anilinolactones was reported. This reaction was performed by using MnFe2O4 nanoparticles (5mol%) as an efficient magnetically heterogeneous catalyst in water as green solvent. Prominent among the advantages of this method is the use of magnetically recoverable and reusable catalyst, simple work up procedure, good to high product yields and use of water as a solvent that is considered to be relatively environmentally benign.

ZnS Nanoparticles: An Efficient Catalyst for the One-Pot Synthesis of Spiro [Pyrrolidine-2, 3'-Oxindole] Derivatives from Phenothiazinyl Chalcones

ZnS-nanoparticles, as recyclable heterogeneous catalyst, efficiently promoted in the synthesis of spiro[pyrrolidine-2,3'-oxindole] derivatives through three-component reaction of isatin, α-amino acid and phenothiazinyl chalcones. An azomethine ylide generated by decarboxylative condensation of isatin with α-amino acid, and chalcones have been used as trapping dipolarophiles. ZnS nanoparticles were synthesized by aqueous chemical method. The advantages of this method lie in its simplicity, cost effectiveness, and easier scaling up for large scale synthesis. Keywords: ZnS-nanoparticles, chalcones, azomethine ylide, multicomponent reaction, spiro-heterocycles.

Recyclization in the Series of Spiro[indole-3,5′-pyrimido[4,5-b]quinoline]-2,2′,4′-triones Prepared by a Three-Component Reaction of Isatins with (Thio)barbituric Acids and Electron-Rich Anilines

A ring–ring transformation in the series of spiro[indole-3,5′-pyrimido[4,5-b]quinoline]-2,2′,4′-trione derivatives prepared by a three-component reaction of (thio)barbituric acids, electron-rich aromatic amines, and isatins was observed.

AcOH catalyzed three-component synthesis of spirooxindole derivatives

An efficient one-pot synthesis of hereto unknown indenoquinoline-spirooxindole derivatives by a three-component reaction of isatins, indan-1,3-dione, and 3-aminocyclohex-2-enone under the catalysis of acetic acid was developed. The procedure had the advantages of simplicity and efficiency.

Organic Reaction in Water: A Highly Efficient and Environmentally Friendly Synthesis of Spiro Compounds Catalyzed by L‐Proline

AbstractWe have developed a clean, simple and efficient method for the synthesis of spiro compounds by three‐component reaction of isatins (=1H‐indole‐2,3‐diones) or acenaphthylene‐1,2‐dione, 1,3‐diphenyl‐1H‐pyrazoles‐5‐amines, and tetronic acid (=furan‐2,4‐(3H,5H)‐dione or 2‐hydroxy‐1,4‐naphthoquinone in the presence of a catalytic amount of L‐proline in aqueous media. The advantages of this procedure are mild reaction conditions, high yields of products, operational simplicity, and easy workup procedures employed.

Efficient One-Pot Synthesis of Novel Spirooxindole Derivatives via Three-Component Reaction in Aqueous Medium

A novel and efficient one-pot synthesis of spiro[indoline-3,4'-pyrazolo[3,4-b]quinoline]dione, spiro[furo[3,4-e]pyrazolo[3,4-b]pyridine-4,3'-indoline]dione, and spiro[indeno[2,1-e]pyrazolo[3,4-b]pyridine-4,3'-indoline]dione derivatives via three-component reaction of isatin, 5-amino-3-methylpyrazole, and 1,3-dicarbonyl compounds in aqueous medium is described. The advantages of this method include high efficiency, mild reaction conditions, convenient operation, and environmentally benign conditions.

Efficient One-Pot Synthesis of Spirooxindole Derivatives Catalyzed byl-Proline in Aqueous Medium

An efficient one-pot synthesis of spirooxindole derivatives by three-component reaction of isatins, malononitrile (cyanoacetic ester) and 1,3-dicarbonyl compounds in water in the presence of l-proline is reported. This new protocol has the advantages of environmental friendliness, higher yields, shorter reaction times, low cost, and convenient operation.

Multicomponent Reaction Discovery: Three-Component Synthesis of Spirooxindoles

The Lewis acid-catalyzed, three-component reaction of isatin and two 1,3-dicarbonyl compounds is reported. Reactions proceed with high efficiency under mild reaction conditions and with good functional group tolerance to afford spirooxindole pyranochromenedione derivatives.

Versatile three-component synthesis of 2′-amino-1,2-dihydrospiro[(3H)-indole-3,4′-(4′H)-pyran]-2-ones

A versatile method for the synthesis of 2′-amino-1,2-dihydrospiro[(3H)-indole-3,4′-(4′H)-pyran]-2-ones has been suggested consisting in the three-component reaction of isatins, cyanoacetic acid derivatives, and α-methylenecarbonyl compounds (β-dicarbonyl compounds, activated phenols, and OH-substituted heterocycles) in ethanol in the presence of triethylamine as a catalyst. The reaction proceeds selectively to form spiro[(3H)-indole-3,4′-(4′H)-pyrans].