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Usage

Uses

Used in Medicinal Chemistry:
1,7-dimethyl-1H-indole-2,3-dione (SALTDATA: FREE) is used as a pharmaceutical candidate for its potential biological activities, such as anti-inflammatory, antimicrobial, antiviral, and anticancer properties. Its diverse applications in medicinal chemistry make it a valuable compound for research and development of new drugs.
Used in Organic Synthesis:
1,7-dimethyl-1H-indole-2,3-dione (SALTDATA: FREE) is used as a key intermediate in organic synthesis for the production of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of complex organic molecules.
Used as a Precursor in Synthesis:
1,7-dimethyl-1H-indole-2,3-dione (SALTDATA: FREE) is used as a precursor in the synthesis of other compounds, particularly in the pharmaceutical and chemical industries. Its availability from natural sources or through chemical reactions makes it a valuable starting material for the production of a wide range of compounds.
Used in Research Applications:
1,7-dimethyl-1H-indole-2,3-dione (SALTDATA: FREE) is used in research settings to study its potential biological activities and explore its applications in various fields. Its unique properties and structure make it an interesting subject for scientific investigation and potential development of new technologies and products.

InChI:InChI=1/C10H9NO2/c1-6-4-3-5-7-8(6)11(2)10(13)9(7)12/h3-5H,1-2H3

Upstream product

• 10541-29-4 2-methyl-N-methylaniline hydrochloride 
• 1233940-50-5 C₁₀H₁₁NO₂ 
• 1013905-81-1 N-methyl-N-(2-methylphenyl)-3-phenylpropynamide 
• 1132-03-2 2-(hydroxyimino)-N-(2-methylphenyl)acetamide 
• 1127-59-9 7-methyl-1H-indole-2,3-dione 
• 74-88-4 methyl iodide 
• 95-53-4 o-toluidine 
• 5621-16-9 1,7-dimethyl-1H-indole 

Downstream Products

• 5621-16-9 1,7-dimethyl-1H-indole 
• 106000-23-1 1,7-Dimethyl-1H-indole-2,3-dione 3-oxime 
• 1604677-01-1 C₁₉H₁₅NO₃ 
• 67358-21-8 1,7-dimethylindolin-2-one 

Relevant academic research and scientific papers

Construction of 2-alkynyl aza-spiro[4,5]indole scaffolds: Via sequential C-H activations for modular click chemistry libraries

Herein, we have developed a strategy of sequential C-H activations of indole to construct novel 2-alkynyl aza-spiro[4,5]indole scaffolds, which incorporated both alkyne and spiro-units into indole. Gram-scale synthesis and a one-pot, three-step synthesis demonstrated the utility of this protocol. Hybrid conjugates with an oseltamivir derivative further offered a powerful tool for the construction of a versatile spiroindole-containing library via click chemistry. This journal is

Annulation reaction of cyclic pyridinium ylides with: In situ generated azoalkenes for the construction of spirocyclic skeletons

Two new types of cyclic pyridinium ylides were designed and further used in reactions with azoalkenes to access structurally diverse spirocyclic compounds. A range of spiropyrazoline oxindoles could be smoothly obtained in up to 99% yield via a [4 + 1] annulation process with oxindole 3-pyridinium ylides as C1 synthons. Similarly, a series of spiropyrazoline indanones could be prepared with indanone 2-pyridinium ylides as C1 synthons. This work represents the first example of cyclic pyridinium ylides as C1 synthons for the efficient construction of spirocyclic compounds.

Transformations of N-arylpropiolamides to indoline-2,3-diones and acids via C≡C triple bond oxidative cleavage and C(sp2)–H functionalization

A new palladium-catalyzed oxidative conversion of N-arylpropiolamides and H2O to various indoline-2,3-diones and acids through the C≡C triple bond cleavage and C(sp2)–H functionalization is described, which is promoted by a cooperative action of catalytic CuBr2, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and O2. The method provides a practical tool for transformations of alkynes by means of a C–H functionalization strategy, which enables the formation of one C–C bond and multiple C–O bonds in a single reaction with high substrates compatibility and excellent functional group tolerance.

Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles

Rationally designed fluorene-based mono- and bimetallic Pd-PEPPSI complexes were synthesized and demonstrated to be effective for the one-pot sequential α-arylation/alkylation of oxindoles. This streamlined approach offers efficient access to functionalized 3,3-disubstituted oxindoles in excellent yields (up to 89%) under mild reaction conditions.

Oxidative Radical Cyclization of N-methyl-N-arylpropiolamide to Isatins via Cleavage of the Carbon-carbon Triple Bond

A radical cyclization of N-methyl-N-arylpropiolamide to isatins via an oxidative cleavage of a carbon-carbon triple bond has been developed. In the presence of oxone and NaNO2, a variety of N-methyl-N-arylpropiolamides were smoothly transformed into isatins. A nitration reaction proceeded along with the oxidative cyclization; both nitrated and non-nitrated isatins were obtained in a one-pot reaction with moderate to good total yields. This is the first example for the synthesis of isatins via the oxidative radical cleavage of a carbon-carbon triple bond. (Figure presented.).

Palladium-Catalyzed Oxidation of Indoles to Isatins by tert -Butyl Hydroperoxide

The combination of a Pd catalyst and tert -butyl hydroeroxide (TBHP) is a powerful catalytic system for many types of oxidative transformations. Here, we report that a Pd/TBHP system facilitates the oxidation of indoles with a range of functionalities to give the corresponding isatin derivatives in good yields.

Direct N-H/α,α,β,β-C(sp3)-H functionalization of piperidine via an azomethine ylide route: synthesis of spirooxindoles bearing 3-substituted oxindoles

A protocol for the direct functionalization of N-H/α,α,β,β-C(sp3)-H of piperidine without any metal or external oxidants is reported. This reaction is promoted by 4-(trifluoromethyl)benzoic acid via an azomethine ylide intermediate. This is a simple method for the synthesis of spirooxindoles bearing 3-substituted oxindole moieties.

Palladium-catalyzed allylic alkylation with internal alkynes to construct C-C and C-N bonds in water

A palladium-catalyzed system enabled efficient allylic alkylation with alkynes in water has been developed. This reaction presents an environmentally friendly strategy for constructing lots of allylic compounds with indolinones, ketones, amines as well as electron-rich aromatic compounds as nucleophiles. Moreover, the in situ formed arylallene intermediate adopting alkynes as starting materials omits the need for leaving groups and extra oxidants, showing high atom economy. The versatility of the developed reaction also lends itself to the incorporation of deuteriums by simply replacing H2O with D2O.

Accessing 1,3-Dienes via Palladium-Catalyzed Allylic Alkylation of Pronucleophiles with Skipped Enynes

An unprecedented palladium-catalyzed allylic alkylation of pronucleophiles with unactivated skipped enynes has been developed. This method provides a straightforward access to a wide array of 1,3-dienes without the need to preinstall leaving groups or employ extra oxidants. The reaction exhibited high atom economy, good functional group tolerance, excellent regioselectivities, and scalability. With D2O as cosolvent, deuterium could be incorporated in high efficiency.

Asymmetric Intermolecular Rauhut?Currier Reaction for the Construction of 3,3-Disubstituted Oxindoles with Quaternary Stereogenic Centers

A remote cross Rauhut?Currier reaction utilizing vinyl ketones and para-quinone methides derived from isatins was realized, which was successfully catalyzed using bifunctional phosphines, furnishing chiral 3,3-disubstituted oxindoles in excellent enantioselectivities and high yields. The mechanistic studies demonstrated the key role of the alkyl hydrogen of the vinyl ketones, which conceivably interacted with the para-quinone methide carbonyl group via the hydrogen bond, offering a new insight for the design of novel asymmetric reactions. (Figure presented.).