1128-44-5

Usage

Uses

Used in Organic Synthesis:
1H-Indole-2,3-dione,4-methylis used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the formation of a wide range of derivatives, making it a valuable building block in the development of new molecules.
Used in Pharmaceutical Chemistry:
1H-Indole-2,3-dione,4-methylis used as a starting material in the synthesis of pharmaceutical compounds. Its presence in the molecular structure can contribute to the biological activity of the final product, potentially leading to the discovery of new drugs.
Note: Since the specifics about the properties of 1H-Indole-2,3-dione,4-methylsuch as boiling point, melting point, density, refractive index, flash point, and its potential applications or risks to health or environment are not well-documented, it is essential to exercise caution when handling and using 1H-Indole-2,3-dione,4-methyl-. Further research and documentation are needed to fully understand its potential applications and risks.

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

Upstream product

• 1132-29-2 2-hydroxyimino-N-m-tolylacetamide 
• 15219-34-8 Oxalyl bromide 
• 108-44-1 1-amino-3-methylbenzene 
• 1388057-45-1 C₉H₇Br₂NO 
• 131543-46-9 Glyoxal 
• 16096-32-5 4-methyl-1H-indole 
• 1189052-03-6 6-methyl-2-nitro-1-[2-iodoethynyl]benzene 
• 401585-34-0 oxalic acid-bis(3-tolylimidoyl)chloride 

Downstream Products

• 20877-81-0 5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 
• 4389-50-8 2-amino-6-methylbenzoic acid 
• 1426932-16-2 C₁₆H₁₃NO₂ 
• 73271-41-7 N-methyl-3-(4-methylphenyl) isatin imine 
• 1608112-09-9 (Z)-4-methyl-3-(2-oxo-2-phenylethylidene)indolin-2-one 

Relevant academic research and scientific papers

Counter-current chromatography separation of isatin derivatives using the sandmeyer methodology

A rapid and efficient method, using high-speed counter-current chromatography (HSCCC) technique, was developed for the separation of isomeric isatin derivatives, prepared following the Sandmeyer route. The biphasic solvent system composed of hexane:ethyl acetate:ethanol:water 1:0.5:0.5:1 (v/v/v/v) was used for all separations.

Excitation-wavelength-dependent photoluminescence of silicon nanoparticles enabled by adjustment of surface ligands

We herein present pioneering studies to reveal that excitation-wavelength-dependent photoluminescence properties of fluorescent silicon nanoparticles (SiNPs) can be realized by rationally designing surface ligands, i.e., several kinds of oxidized indole d

Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides

Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.

Method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid

The invention discloses a method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid. The method comprises the following steps: a catalytic amount of catalyst copper iodide, indole, a derivative of the indole and peroxyacetic acid are added into a reaction vessel, wherein the indole, the derivative of the indole and the peroxyacetic acid are usedas raw materials, ethanol is used as a solvent, the reaction vessel is placed into a microwave reaction instrument, a reaction is performed at certain temperature and power, after a certain time, reduced-pressure concentration is performed, and a product is purified by column chromatography. The method provided by the invention is a method having novel raw materials, simple operation and high efficiency used for preparing a benzimidazole derivative; and compared with the prior art, the method provided by the invention has an obviously-accelerated reaction speed than that under conventional heating, mild reaction conditions, simple operation, a high yield, safety, low costs and environmental protection.

Double Carbonylation Using Glyoxal (HCOCOH): A Practical Copper-Promoted Synthesis of Isatins from Primary and Secondary Anilines

A novel double carbonylation process has been demonstrated with easily available HCOCOH (glyoxal) as the double carbonylation reagent. Simple CuCl2?2H2O (copper(II) chloride dihydrate) was used as the oxidant for this transformation. Under optimized reaction conditions, various primary and secondary anilines were double-carbonylated to afford their corresponding isatins (26 examples, up to 80% yields). (Figure presented.).

Synthesis of isatins by I2/TBHP mediated oxidation of indoles

An I2/TBHP mediated oxidation of commercially available indoles has been developed, which affords isatins in moderate to good yields.

Extended structure-activity relationship and pharmacokinetic investigation of (4-quinolinoyl)glycyl-2-cyanopyrrolidine inhibitors of fibroblast activation protein (FAP)

Fibroblast activation protein (FAP) is a serine protease related to dipeptidyl peptidase IV (DPPIV). It has been convincingly linked to multiple disease states involving remodeling of the extracellular matrix. FAP inhibition is investigated as a therapeutic option for several of these diseases, with most attention so far devoted to oncology applications. We previously discovered the N-4-quinolinoyl-Gly-(2S)-cyanoPro scaffold as a possible entry to highly potent and selective FAP inhibitors. In the present study, we explore in detail the structure-activity relationship around this core scaffold. We report extensively optimized compounds that display low nanomolar inhibitory potency and high selectivity against the related dipeptidyl peptidases (DPPs) DPPIV, DPP9, DPPII, and prolyl oligopeptidase (PREP) the log D values, plasma stabilities, and microsomal stabilities of selected compounds were found to be highly satisfactory. Pharmacokinetic evaluation in mice of selected inhibitors demonstrated high oral bioavailability, plasma half-life, and the potential to selectively and completely inhibit FAP in vivo.

Ylide mediated carbonyl homologations for the preparation of isatin derivatives

An exceptionally mild method for the preparation of isatin derivatives has been developed using a sulfur ylide mediated carbonyl homologation sequence starting from anthranilic acid precursors. This method proceeds at ambient temperature via a sulfur ylide intermediate without the need for protection of the amine or chromatographic isolation of the intermediate ylide. Gentle oxidation of the sulfur ylides provides isatin derivatives with N-H, N-alkyl, N-aryl substitution, electron-rich and electron-poor aromatic rings, and heterocyclic aromatic systems. We anticipate that this method will greatly expand the accessibility of complex isatin derivatives.

Structure-based design and parallel synthesis of N-benzyl isatin oximes as JNK3 MAP kinase inhibitors

A series of N-benzylated isatin oximes were developed as inhibitors of the mitogen-activated kinase, JNK3. X-ray crystallographic structures aided in the design and synthesis of novel, selective compounds, that inhibit JNK3, but not p38 MAP kinase and provided key insights into understanding the behavior of gatekeeper residue methionine-146 in determining target selectivity for this series.

A palladium-catalyzed synthesis of isatins (1H-Indole-2,3-diones) from 1-(2-haloethynyl)-2-nitrobenzenes

An inherently regiospecific synthesis of isatins (1H-indole-2,3-diones) starting from 1-halo-2-nitrobenzenes is described. The isatins are formed by an intramolecular palladium-catalyzed annulation of 2-(2-haloethynyl)-1-nitrobenzenes via the formation of 2-haloisatogens.