14003-18-0

Upstream product

• 59-48-3 2-oxoindole 
• 105-56-6 ethyl 2-cyanoacetate 
• 91-56-5 indole-2,3-dione 
• 13504-72-8 triphenylphosphorane 

Downstream Products

• 210232-93-2 ethyl 2-amino-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carboxylate 
• 74647-44-2 5'-acetyl-2'-amino-3'-ethoxycarbonyl-6'-methylspiro-2-one 
• 2365-44-8 (3Z)-1H-Indole-2,3-dione 3-hydrazone 
• 2365-44-8 (E)-3-hydrazonoindolin-2-one 
• 607-28-3 Isatin-3-oxime 
• 1431523-31-7 ethyl 2-amino-1-(3-chlorophenyl)-2',5-dioxo-1,5-dihydrospiro[indeno[1,2-b]pyridine-4,3'-indoline]-3-carboxylate 
• 1431523-30-6 ethyl 2-amino-1-phenylamino-2',5-dioxo-1,5-dihydrospiro[indeno[1,2-b]pyridine-4,3'-indoline]-3-carboxylate 
• 75459-99-3 spiro 
• 75459-99-3 spiro 
• 75459-98-2 spiro 
• 14003-19-1 ethyl cyano-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)acetate 
• 106536-40-7 ethyl 6′-amino-3′-methyl-2-oxo-1′-phenyl-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carboxylate 
• 83451-58-5 2-Amino-3-ethoxycarbonyl-4-quinolyl-1-phenyl-5-oxo-2-pyrazolin-4-yl ketone 
• 75459-96-0 3-(carboethoxy-cyano)methyl-3-phenacyloxindole 

Relevant academic research and scientific papers

Synthetic and Theoretical Studies on the Reduction of Electron Withdrawing Group Conjugated Olefins Using the Hantzsch 1,4-Dihydropyridine Ester

The Hantzsch 1,4-dihydropyridine ester (1) has been observed to be a useful selective reducing agent for the reduction of electron-withdrawing conjugated double bonds. The rate of this reaction was observed to be dependent upon the nature of the conjugate

Ionic Liquid Mediated Green Synthesis of Spirooxindoles from N-methyl Quinolones and Their Anti Bacterial Activity

Three-component reaction involving condensation of 1-methyl quinoline-2,4(1H,3H)-dione 1, isatins 2(a–e), and malononitrile/cyanoacetic ester 3(a–b) in the task-specific ionic liquid [DBU][Ac] (1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate) leading to the spirooxindole derivatives 4(a–j) is described. This approach is affords the products in high yields without use of column chromatography and resulting compounds were evaluated for antibacterial activity against both gram positive and gram negative bacteria (Staphylococcus aureus, Escherichia coli, Bacillus cereus, Bacillus subtilis, Salmonella typhimurium, and Klebsiella pneumonia). Among the all compounds, four compounds, that is, 4b, 4e, 4f, 4g, 4j exhibited moderate activity against all the strains as compared with the standard used.

Bioreduction of the C=C double bond with Pseudomonas monteilii ZMU-T17: One approach to 3-monosubstituted oxindoles

An efficient whole cell-mediated bioreduction of 3-methylene-2-oxindoles has been developed, affording a range of 3-monosubstituted oxindoles in moderate to good yields (41-82%) with Pseudomonas monteilii ZMU-T17 as biocatalyst. Additionally, a possible reaction pathway for this bioreduction of C=C double bond was proposed.

TiCl4/DMAP mediated: Z -selective knovenagel condensation of isatins with nitroacetates and related compounds

A highly efficient Z-selective Knovenagel condensation reaction of isatins with nitroacetates mediated by TiCl4 and DMAP was described. The desired 2-nitro-3-ylideneoxindole acetates were obtained in good to excellent stereoselectivities and yields. Other activated methylene derivatives as well as 4-methylbenzenesulfonamide could provide good results too. This method makes it possible to obtain various unreported 3-ylideneoxindole derivatives under mild reaction conditions.

Synthesis of 2,6′-dioxo-1′,5′,6′,7′- tetrahydrospiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-5′- carbonitriles via a one-pot, three-component reaction in water

A one-pot, three-component condensation reaction of an isatin, aminopyrazole, and alkyl cyanoacetate in water to give 2,6′-dioxo- 1′,5′,6′,7′-tetrahydrospiro[indoline-3, 4′-pyrazolo[3,4-b]pyridine]-5′-carbonitrile with good yields, at 90 C, using a Et3N as catalyst, is described.

Reaction of isatins with active methylene compounds on neutral alumina: Formation of knoevenagel condensates and other interesting products

Isatin and its N-methyl and 5-nitro derivatives underwent smooth reaction with a variety of acyclic and cyclic active methylene compounds on neutral alumina at rt to efficiently furnish Knoevenagel condensates in the majority of the cases and tandem Knoevenagel condensation-Michael addition products including spiro compounds in two cases.

Iron-catalyzed cross-dehydrogenative coupling of indolin-2-ones with active methylenes for direct carbon-carbon double bond formation

The iron-catalyzed cross-dehydrogenative coupling (CDC) of C(sp3)-H/C(sp3)-H bonds to afford olefins by 4H elimination is described. This method employs air (molecular oxygen) as an ideal oxidant, and is performed under mild, ligand-free and base-free conditions. H2O is the only byproduct. Good tolerance of functional groups and high yields have also been achieved. Preliminary mechanistic investigations suggest that the present transformation involves a radical process.

Synthesis of spiro[2,3-dihydrofuran-3,3′-oxindole] derivatives: Via a multi-component cascade reaction of α-diazo esters, water, isatins and malononitrile/ethyl cyanoacetate

We report a green synthesis of spiro[2,3-dihydrofuran-3,3′-oxindole] derivatives which are of potential value in medicinal chemistry. We are able to access spiro[2,3-dihydrofuran-3,3′-oxindole] derivatives via a Cu(OTf)2-catalyzed or Cu(OTf)2/Rh2(OAc)4-cocatalyzed multi-component cascade reaction of α-diazo esters, water, isatins and malononitrile/ethyl cyanoacetate. The reaction can be accomplished in good to excellent yields (60-99%), and the structure of products 6a and 6k was supported by X-ray crystallography. The catalyst Cu(OTf)2 can be recycled 4 times without a sharp loss of the yield of 6a. 6q can be easily synthesized in gram scale. In brief, the reaction is characterized by step economy, a harmless solvent, and a recyclable catalyst.

Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast

3-Substituted oxindoles are very interesting molecules both for their potential biological activity and for their role as starting materials toward more complex oxindole-based structures. These molecules can be prepared by the reduction of a 3-ylidene oxi

Knovenagel condensation of isatin with nitriles and 1, 3-diketones

Knoevenagel condensation of isatin 1 with some nitriles 2 and with cyclohexane-1,3-diones 4 using piperidinium acetate as catalyst in water at 100°C results in the formation of α,β - unsaturated products, i.e. 2-(2-oxo-1,2-dihydro-indol-3- ylidene)-malono