53904-10-2

Upstream product

• 948-65-2 2-phenyl-indole 
• 96-96-8 4-methoxy-2-nitroaniline 
• 67-56-1 methanol 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 13141-38-3 2-phenylethynylaniline 
• 6127-43-1 2-Phenyl-3-oxindol 
• 2989-63-1 2-phenyl-3H-indol-3-one 
• 105-53-3 diethyl malonate 

Downstream Products

• 1969-74-0 2-phenylisatogen 

Relevant academic research and scientific papers

Selective synthesis of 2-indolyl-3-oxoindolines or 2-(2-aminophenyl)quinolines through Cu(II)- or Bi(III)-catalyzed tunable dimerizations of 2-alkynylanilines

A novel and selective synthesis of 2-indolyl-3-oxoindolines or 2-(2-aminophenyl)quinolines through tunable dimerizations of 2-alkynylanilines is presented. Mechanistically, the formation of 2-indolyl-3-oxoindolines involves a Cu(OAc)2/O2-promoted intramolecular cyclization of 2-alkynylaniline to give the required indole and 3H-indol-3-one intermediates followed by the indolylation of 3H-indol-3-one. On the other hand, the formation of 2-(2-aminophenyl)quinolines is believed to go through a Bi(OTf)3/MesCO2H-catalyzed intermolecular N-nucleophilic addition between two 2-alkynylaniline molecules to give an enamine intermediate followed by its intramolecular C-nucleophilic addition/annulation. Notable features of these new methods include easily obtainable substrates, economical catalysts and oxidant, controllable selectivity, and high versatility toward diverse products.

Gold/Copper-Co-catalyzed Tandem Reactions of 2-Alkynylanilines: A Synthetic Strategy for the C2-Quaternary Indolin-3-ones

A new strategy for direct and highly efficient synthesis of 2,3′-bisindolin-3-ones has been developed via a gold/copper-co-catalyzed tandem reactions of 2-alkynylanilines using TBHP as the terminal oxidant and oxygen-atom source. The single-step process involves a novel tandem intermolecular nucleophilic addition, intramolecular cyclization/oxidative cross-dehydrogenative coupling where up to four new bonds and two indole rings were created simultaneously in one-pot manner. The reaction features a broad substrate scope, good functional group tolerance, and high atom-economy.

Synthesis of C2-tetrasubstituted indolin-3-ones via Cu-catalyzed oxidative dimerization of 2-aryl indoles and cross-addition with indoles

An efficient protocol for the synthesis of 2,2-disubstituted indolin-3-ones under mild conditions has been developed. This reaction involves the copper-catalyzed in situ oxidative de-aromatization of 2-arylindoles to indol-3-one, followed by self-dimeriza

Ruthenium-Catalyzed Oxidative Dearomatization of Indoles for the Construction of C2-Quaternary Indolin-3-ones

A ruthenium-catalyzed oxidative dearomatization of 2-alkyl- or 2-aryl-substituted indoles has been developed. When coupled with a cascade transformation, it provides a new system for the construction of indolin-3-ones bearing a C2-quaternary functionality

Auto-tandem PET and EnT photocatalysis by crude chlorophyll under visible light towards the oxidative functionalization of indoles

Chlorophyll is the most abundant photocatalytic pigment that enables plants to absorb solar energy and convert it to energy storage molecules. Herein, we report a tandem photocatalytic approach utilizing the natural pigment chlorophyll in crude form to achieve photoinduced electron transfer (PET) and energy transfer (EnT) towards the oxidative functionalization of indoles. Redox potentials, ESR, fluorescence quenching and UV experiments have evidenced the dual catalytic activity of chlorophyll. The highlight of the study is the auto-tandem photocatalytic role of chlorophyll to enable the green oxidation of indoles using molecular oxygen as the oxidant, water as the reaction medium, and photochemical energy from the visible region of the spectrum.

Oxidative dearomative cross-dehydrogenative coupling of indoles with diverse C-H nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones

The oxidative, dearomative cross-dehydrogenative coupling of indoles with various C-H nucleophiles is developed. This process features a broad substrate scope with respect to both indoles and nucleophiles, affording structurally diverse 2,2-disubstituted indolin-3-ones in high yields (up to 99%). The oxidative dimerization and trimerization of indoles has also been demonstrated under the same conditions.

Synthesis method of 2-indole-3-oxoindoline compound

The invention discloses a synthesis method of a 2-indole-3-oxoindoline compound, and belongs to the technical field of organic synthesis. The synthesis method comprises the following steps: mixing a 2-alkynyl aniline compound 1, a bivalent copper salt catalyst and a solvent, and carrying out a heating reaction in an oxygen-containing atmosphere to obtain the 2-indole-3-oxoindoline compound 2. According to the preparation method disclosed by the invention, the 2-indole-3-oxoindoline compound is synthesized in one step through an intermolecular dimerization reaction of the 2-alkynyl aniline compound. The method has the advantages of cheap and easily available raw materials, mild reaction conditions, wide substrate application range, high atom economy of the reaction and the like, meets the development requirements of modern green chemistry, and provides an efficient and practical new method for synthesizing the 2-indole-3-oxoindoline compound.

Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch

An efficient chemodivergent strategy for visible light photocatalysis is developed. In the presence of a dicyanopyrazine-derived chromophore (DPZ) photocatalyst, aerobic photooxygenation of indoles could produce either isatins or formylformanilides in satisfactory yields by judiciously selecting inorganic salts or modulating the reaction pH. The current chemodivergent method is also effective with 2-substituted indoles, opening straightforward synthetic routes to valuable 2,2-disubstituted 3-oxindoles, formylformanilide derivatives, and benzoxazinones. Mechanistic investigations involving cyclic voltammetry studies further confirm that reaction pH influences the electrochemical properties of DPZ, thus affecting the oxidative pathway by which indoles are being transformed.

Silver-catalyzed TEMPO oxidative homocoupling of indoles for the synthesis of 3,3′-biindolin-2-ones

An oxidative homo dimerization of free indole derivatives, by means of silver catalysis and TEMPO oxidant, was first successful demonstrated. This new methodology is both atom and step efficient and is applicable to a broad scope of substrates, allowing the synthesis of a range of synthetically valuable substituted C3-C3′ bisindolin-2-ones in moderate to excellent yields.

Copper-catalyzed oxidative trimerization of indoles by using TEMPO to construct quaternary carbon centers: The synthesis of 2-(1 H -indol-3-yl)-2,3′-biindolin-3-ones

A simple, convenient, and efficient synthesis of 2-(1H-indol-3-yl)-2, 3′-biindolin-3-one derivatives has been developed by the oxidative trimeric reaction of indoles using the TEMPO/CuCl2 catalyst system under ambient air. This methodology provides an alternative approach for the direct generation of all-carbon quaternary centers at the C-2 position of indoles.