1127-59-9

Usage

Uses

Used in Pharmaceutical Synthesis:
7-METHYL-1H-INDOLE-2,3-DIONE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form a wide range of biologically active compounds, contributing to the development of new medications.
Used in Forensic Science:
In the field of forensic science, 7-METHYL-1H-INDOLE-2,3-DIONE is used as a color developing agent for the detection of latent bloodstains, capitalizing on its distinctive blue fluorescence to aid in crime scene investigations.
Used in Antimicrobial Applications:
7-METHYL-1H-INDOLE-2,3-DIONE is utilized as an antimicrobial agent for its antiviral, antifungal, and antibacterial properties, making it a potential candidate for the development of novel drugs to combat various infectious diseases.
Used in Cancer Therapy Research:
In the realm of oncology, 7-METHYL-1H-INDOLE-2,3-DIONE is being studied for its potential role in cancer therapy, exploring its capacity to target and treat cancer cells, possibly leading to the creation of innovative cancer treatments.
Used in Organic Synthesis as a Precursor:
7-METHYL-1H-INDOLE-2,3-DIONE is used as a precursor in the synthesis of organic molecules with biological activity, highlighting its importance in the creation of new compounds with potential applications in various industries, including pharmaceuticals and materials science.

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

Upstream product

• 79-37-8 oxalyl dichloride 
• 636-21-5 o-toluidine hydrochloride 
• 1132-03-2 2-(hydroxyimino)-N-(2-methylphenyl)acetamide 
• 135850-46-3 N,N'-bis(2-methylphenyl)ethane-bis(imidoyl) dichloride 
• 1066-30-4 chromium(lll) acetate 
• 859076-14-5 1-benzoyl-7,7'-dimethyl-1H,1'H-[2,2']biindolylidene-3,3'-dione 
• 40800-67-7 7-methyl-3-methylsulfanyl-1,3-dihydro-indol-2-one 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 67-56-1 methanol 
• 861309-54-8 2-hydroxy-7,7'-dimethyl-1-nitroso-1,2,1',2'-tetrahydro-[2,2']biindolyl-3,3'-dione 
• 64-17-5 ethanol 
• 6371-32-0 (E)-7,7'-dimethyl-1H,1'H-[2,2']biindolylidene-3,3'-dione 
• 4053-36-5 8-Methyl-2-hydroxyquinoline 

Downstream Products

• 63220-45-1 3-hydroxy-7-methyl-3-phenyl-indolin-2-one 
• 511241-69-3 2,8-dimethyl-quinoline-4-carboxylic acid amide 
• 13208-96-3 7-methylisatin-3-oxime 
• 77395-10-9 5-bromo-7-methyl-2,3-d1H ydro-1H-indole-2,3-dione 
• 4389-45-1 3-methylantranilic acid 
• 859770-30-2 (2-amino-3-methyl-phenyl)-glyoxylic acid 
• 107027-39-4 8-Methyl-2-pyridin-3-yl-quinoline-4-carboxylic acid 
• 113431-41-7 8-methyl-3-phenylquinoline-2,4-dicarboxylic acid 
• 219660-86-3 7-methyl-3-[(3-phenyl-[1,8]naphthyridin-2-yl)-hydrazono]-1,3-dihydro-indol-2-one 
• 261631-65-6 2-Phenyl-[1,8]naphthyridine-3-carboxylic acid [7-methyl-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide 
• 70343-13-4 7-methyl-5-nitro-1H-indole-2,3-dione 
• 56632-39-4 7-methyl-oxyphenisatine 
• 261631-74-7 C₂₆H₁₉N₅O₃S 
• 113431-42-8 8-methyl-3-phenylquinoline 

Relevant academic research and scientific papers

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.).

Combretastatin A-4 analogues with benzoxazolone scaffold: Synthesis, structure and biological activity

In order to design and synthesize a new class of heterocyclic analogues of natural combretastatin A-4 and its synthetic derivative AVE8062, the benzoxazolone ring was selected as a scaffold for a bioisosteric replacement of the ring B of both molecules. A library of 28 cis- and trans-styrylbenzoxazolones was obtained by a modified Wittig reaction under Boden's conditions. Structures of the newly synthesized compounds bearing the 3,4,5-trimethoxy-, 3,4-dimethoxy-, 3,5-dimethoxy-, and 4-methoxystyryl fragment at position 4, 5, 6 or 7 of benzoxazolone core were determined on the basis of spectral and X ray data. The in vitro cytotoxicity of styrylbenzoxazolones against different cell lines was examined. Stilbene derivative 16Z, (Z)-3-methyl-6-(3,4,5-trimethoxystyryl)-2(3H)-benzoxazolone, showed highest antiproliferative potential of the series, with IC50 of 0.25 μM against combretastatin resistant cell line HT-29, 0.19 μM against HepG2, 0.28 μM against EA.hy926 and 0.73 μM against K562 cells. Furthermore, the results of flow cytometric analysis confirmed that 16Z induced cell cycle arrest in G2/M phase in the cell lines like combretastatin A-4. This arrest is followed by an abnormal exit of cells from mitosis without cytokinesis into a pseudo G1-like multinucleate state leading to late apoptosis and cell death. Accordingly, synthetic analogue 16Z was identified as the most promising potential anticancer agent in present study, and was selected as lead compound for further detailed investigations.

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.

Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipole and Abnormal [3 + 2]-Cycloaddition with Maleimide in the Presence of 1,4-Diazabicyclo[2.2.2]octane

A new isatin N,N′-cyclic azomethine imine synthon was devised, and an unexpected abnormal [3 + 2]-cycloaddition with maleimide catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) has been disclosed. A variety of tricyclic spiropyrrolidine oxindoles bearing a dinitrogen heterocycle and succinimide scaffold were obtained in excellent yields (up to 96%) and diastereoselectivities (up to 97:3) under mild conditions.

Entry into the bi-aryl moiety of the TMC-95 proteasome inhibitors via the Stille protocol

The synthesis of the bi-aryl moiety of the TMC-95 natural products has been achieved via a palladium-catalyzed Stille cross-coupling reaction of an aryl stannane tyrosine derivative and 7-iodoisatin.

Study on synthesis of some substituted N-propargyl isatins by propargylation reaction of corresponding isatins using potassium carbonate as base under ultrasound- and microwave-assisted conditions

Substituted N-propargyl isatins were synthesized by SN2 reaction of corresponding substituted isatins with propargyl bromide in the presence of anhydrous K2CO3 as base. We reported about study on systematically synthesis of these compounds using heating procedures under different reaction conditions, including microwave-assisted heating conditions at power of 100?W (Procedure A), conventional heating conditions in water bath at 50?°C in acetonitrile (Procedure B), and conventional heating conditions in water bath at 50?°C in DMF (procedure C). The best procedure A was deduced based on the investigations on the reaction conditions. Almost all substituted N-propargyl isatins were new, except compounds with R of H, 5-Me, 5-Cl and 5-Br substituents. The structures of the obtained compounds were confirmed by the modern spectroscopic methods.

Single step regioselective cyclization and chlorination of hydroxyamino-N-(2-methylphenyl)acetamide to 5-chloro-7-methylindoline-2,3-dione

A one-pot process for the manufacture of 5-chloro-7-methylindoline-2,3-dione starting from 2-hydroxyimino-N-(2-methylphenyl)acetamide via tandem cyclization in sulfuric acid and acetic acid, followed by in-situ chlorination with sulfur dioxide and chlorine gas in high regioselectivity and yield.

AN EFFICIENT NEW PROCESS FOR SYNTHESIS OF 2-AMINO-5-CHLORO-N-,3-DIMETHYLBENZAMIDE

Described herein are novel methods of synthesizing 2-amino-5-chloro-N,3- dimethylbenzamide. Compounds prepared by the methods disclosed herein are useful for preparation of certain anthranilamide compounds that are of interest as insecticides, such as, for example, the insecticides chlorantraniliprole and cyantraniliprole.

A PROCESS FOR PREPARING ANTHRANILIC DIAMIDES AND INTERMEDIATES THEREOF

The present invention relates a novel process for preparing a compound of Formula I, wherein, R1, R2, R3a, R3b, R3c, R4, R5, R6, R7 and Z are as defined in the description. The process comprises a novel and inventive step of converting a dione of Formula II into an isatoic anhydride of Formula V in a single step, wherein, R2 is F, Cl, Br or I; R1, R3a, R3b, R3c, R4, R5, R6, R7 and Z are as defined in the description.

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.