2058-74-4

Usage

Uses

Used in Pharmaceutical Industry:
N-METHYLISATIN is used as a reactant for the stereoselective preparation of spirobicyclic and bis-spirotricyclic pyrazolidinones, which are important in the development of pharmaceutical compounds with specific biological activities.
Used in Organic Synthesis:
N-METHYLISATIN is used as a reactant for the regioselective preparation of spirocyclic oxindole-butenolides, which are valuable intermediates in the synthesis of bioactive molecules.
Used in the Synthesis of Spiro-Oxindoles:
N-METHYLISATIN is used as a reactant for the synthesis of spiro-oxindoles, a class of compounds with potential applications in medicinal chemistry.
Used in the Preparation of Unsymmetrical Oxindoles:
N-METHYLISATIN is used as a reactant for the preparation of unsymmetrical oxindoles, which are important building blocks in the synthesis of various biologically active compounds.
Used in the Stereoselective Preparation of Hydroxyloxindoles:
N-METHYLISATIN is used as a reactant for the stereoselective preparation of hydroxyloxindoles via the Morita-Baylis-Hillman reaction, a versatile method for the synthesis of chiral molecules.
Used in the Preparation of Pyridinecarboxylic Acid Derivatives:
N-METHYLISATIN is used as a reactant for the preparation of pyridinecarboxylic acid [(oxo)indolylidene)hydrazide derivatives (Schiff base hydrazides), which have potential applications as antibacterial agents.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 47, p. 2089, 2004 DOI: 10.1021/jm030483s

InChI:InChI=1/C9H7NO2/c1-10-7-5-3-2-4-6(7)8(11)9(10)12/h2-5H,1H3

Upstream product

• 91-56-5 indole-2,3-dione 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 60-29-7 diethyl ether 
• 61-70-1 N-methyl-2-indolinone 
• 1677-46-9 4-hydroxy-1-methyl-2(1H)-quinolone 
• 16526-19-5 (E)-1,4-dibromo-2-methylbut-2-ene 
• 1912-48-7 2-(1-methyl-1H-indol-3-yl)acetic acid 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 91658-90-1 1-N-methyl-3-(2-aminophenylimino) indoline 2-one 
• 76325-64-9 3-hydroxy-1-methyl-3-(2'-oxopropyl)indolin-2-one 
• 7647-01-0 hydrogenchloride 
• 3335-86-2 3-hydroxy-1-methyl-indolin-2-one 
• 7732-18-5 water 

Downstream Products

• 97207-47-1 (E)-1-methyl-[3,3'-biindolinylidene]-2,2'-dione 
• 15757-32-1 3-hydroxy-1-methyl-3-phenyl-1,3-dihydro-2H-indol-2-one 
• 81235-51-0 1-methyl-2,2-diphenyl-indolin-3-one 
• 22136-54-5 N-methyl-1,3-dihydro-3,3-diphenyl-2H-indol-2-one 
• 75-07-0 acetaldehyde 
• 60463-77-6 1-methyl-3-hydroxy-3-(2-oxo-2-phenylethyl)indolin-2-one 
• 65880-39-9 1-N-methyl-indolo <2,3-b> quinoxaline 
• 15096-16-9 N-Methylisatin 3-phenylhydrazone 
• 108124-50-1 1-methyl-3-(2-oxo-5-phenyl-furan-3-ylidene)-indolin-2-one 
• 3265-24-5 (E)-3-(hydroxyimino)-1-methylindolin-2-one 
• 3484-32-0 1-methyl-5-nitro-1H-indole-2,3-dione 
• 119-68-6 N-Methylanthranilic acid 
• 3265-23-4 1-methyl-3-hydrazinoisatin 
• 83393-57-1 3-Hydroxy-1-methyl-3-(2-oxo-2-pyridin-4-yl-ethyl)-1,3-dihydro-indol-2-one 

Relevant academic research and scientific papers

Synthesis of novel 5-substituted indirubins as protein kinases inhibitors

In an effort to identify new pharmacological inhibitors of disease-relevant protein kinases with increased potency and selectivity, we synthesized and evaluated new 5-substituted indirubins. The effects of 34 indirubin derivatives on CDK1/cyclin B, CDK5/p25, and GSK-3, as well as on SH-SY5Y human neuroblastoma cell survival, were investigated.

Synthesis of new 3-(Trifluoromethyl)-1H-indoles by reduction of trifluoromethyloxoindoles

(Chemical Equation Presented) This work describes the synthesis of new 3-trifluoromethylindoles. Different isatins were trifluoromethylated using (trifluoromethyl)trimethylsilane (Me3SiCF3) as a nucleophilic agent giving new 3-hydroxy-3-(trifluoromethyl)indolin-2-one. Different "one-step" procedures to transform the latter compounds into the reduced indoles were attempted, but failed. For the synthesis of the new trifluoromethylindoles the corresponding 2-oxo-3-(trifluoromethyl)indoles were reduced using borane/THF complex to furnish 3-(trifluoromethyl)indolin-3-ol that additionally were dehydrated using thionyl chloride in pyridine to give excellent yields of the desired products.

AcOH-mediated dichloroimination of indoles using chloramine-B: A facile access to 2,3-functionalized indolines

A new and mild method for the efficient synthesis of 3,3-dichloro-2-sulfonyliminoindolines via AcOH-mediated dichloroimination of indoles using chloramine-B is presented. Application of this method to the efficient construction of pyrrolidinoindoles and N-C3 linked pyrrolidinoindolines is demonstrated.

Formation of indole trimers in Vilsmeier type reactions

The reaction of indole with the complex formed from 1,3-dimethylimidazolidin-2-one or N-methyloxindole with phosphorus oxychloride (phosphoryl chloride), was studied. In similar reactions of five-membered tertiary amide rings, 3-(1-alkyl-pyrrolidin-2-ylidene)-3H-indoles or ring opening products were obtained but in these cases, new products N1,N2-dimethyl-N1-[tri-(1H-indol-3-yl)methyl]ethane-1,2-diamine and N-methyl-2-(3,3,3-tri-(1H-indol-3-yl)propyl)aniline as trimers of indole were obtained. (Formula presented).

C-H Activation Relay (CHAR): An Efficient Construction of Isatin Skeleton by Aerobic Oxidation of Glycine Esters

Directed by the strategy of C-H activation relay (CHAR), an efficient construction of isatin skeleton was developed through catalytic oxidation of glycine esters. The mechanistic study reveals that the oxidation of the relatively active C-H bonds initiated the followed activation of remote and inert C-H bonds, and an intramolecular 1,6-hydrogen shift was involved as a key step.

Novel indolin-2-one-substituted methanofullerenes bearing long N-alkyl chains: Synthesis and application in bulk-heterojunction solar cells

An easy, high-yield and atom-economic procedure of a C60 fullerene modification using a reaction of fullerene C60 with N-alkylisatins in the presence of tris(diethylamino)phosphine to form novel long-chain alkylindolinone-substituted methanofullerenes (AIMs) is described. Optical absorption, electrochemical properties and solubility of AIMs were studied. Poly(3-hexylthiophene-2,5-diyl) (P3HT)/AIMs solar cells were fabricated and the effect of the AIM alkyl chain length and the P3HT:AIM ratio on the solar cell performance was studied. The power conversion efficiencies of about 2% were measured in the P3HT/AIM devices with 1:0.4 P3HT:AIM weight ratio for the AIMs with hexadecyl and dodecyl substituents. From the optical and AFM data, we suggested that the AIMs, in contrast to [6,6]-phenyl-C61-butyric acid methyl ester (PCBM), do not disturb the P3HT crystalline domains. Moreover, the more soluble AIMs do not show a better miscibility with the P3HT crystalline phase.

New and efficient one-pot synthesis of functionalized γ-spirolactones mediated by vinyltriphenylphosphonium salts

The addition of dimethyl acetylenedicarboxylate to isatin derivatives in the presence of triphenylphosphine leading to new highly functionalized γ-spirolactones is reported.

Aqueous tert-Butyl Hydroperoxide Mediated Regioselective Ring-Opening Reactions of Spiro-aziridine-epoxy Oxindoles: Synthesis of 3-Peroxy-3-substituted Oxindoles and Their Acid-Mediated Rearrangement

A highly efficient regioselective C3-peroxylation of spiro-aziridine and spiro-epoxy oxindoles has been developed with commercially available 70% aqueous tert-butyl hydroperoxide under solvent-free and metal/catalyst-free conditions. The protocol provides an easy access of 3-peroxyoxindoles, which undergo acid-mediated rearrangement to afford unprecedented 2-hydroxy-2-substituted-2H-benzo[b][1,4]oxazin-3(4H)-ones. The protocol is also equally effective for the ring opening of simple phenyl aziridine with excellent regio-selectivity.

First X-ray structural characterization of isatin Schiff base derivative. NMR and theoretical conformational studies

Isatin (1H-indole-2,3-dione) is an endogenous natural compound under intense development in medicinal chemistry. Here, we characterize isatin Schiff base derivative by X-ray crystallography. We describe a derivative that crystallizes E-isomer form in the triclinic space group P 1ˉ; a = 5.9580 (4) A?, b = 8.4184 (7) A?, c = 14.1801 (14) A?, α = 73.962 (8)°, β = 83.184 (7)°, γ = 81.143 (6)°. NMR data show that E-conformer interconverts to the Z-conformer when dissolved, this equilibrium weakly depends on the solvent type. The Z-isomer geometry and the energetics of ΔEE-Zinterconversion barriers were determined by quantum chemical calculations. The isomers are further characterized by means of FT-IR and UV-Vis spectroscopy.

Reaction of 1-substituted 3-(2-hydroxyethylamino)quinoline-2,4(1H,3H)-diones with isothiocyanic acid

[Figure not available: see fulltext.] 3-Chloroquinoline-2,4-diones react with ethanolamine to form 3-(3-hydroxyethylamino)quinoline-2,4-diones. These compounds afford, depending on substituents in positions 1 and 3, four different products from their reac