7466-59-3

Usage

Uses

Used in Pharmaceutical Industry:
2,3-dimethyl-3-phenyl-3H-indole is used as a key intermediate in the synthesis of various pharmaceuticals for its potential therapeutic properties. It has been studied for its anticancer, antimicrobial, and anti-inflammatory effects, which contribute to the development of new drugs targeting these conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 2,3-dimethyl-3-phenyl-3H-indole is used as a building block in the creation of agrochemicals. Its chemical properties allow it to be incorporated into compounds that can be used for pest control and crop protection, enhancing agricultural productivity.
Used in Organic Materials Synthesis:
2,3-dimethyl-3-phenyl-3H-indole is utilized as a precursor in the synthesis of organic materials. Its unique structure and reactivity enable the production of advanced materials with specific properties, such as in the fields of electronics, optics, and materials science, where novel compounds with tailored characteristics are constantly sought after.

Upstream product

• 190788-59-1 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 615-36-1 2-bromoaniline 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 27309-58-6 1-(2-Amino-phenyl)-2-methyl-1-phenyl-prop-1-en 
• 91-55-4 2,3-dimethylindole 
• 108-90-7 chlorobenzene 
• 100-63-0 phenylhydrazine 
• 611-70-1 phenyl isopropyl ketone 

Downstream Products

• 73822-16-9 2,3-dimethyl-3-phenylindoline 
• 73822-16-9 2,3-dimethyl-3-phenylindoline 
• 51167-76-1 2,3-dihydro-1,3-dimethyl-2-methylene-3-phenyl-1H-indole 
• 51167-73-8 l'iodure de 1,2,3-trimethyl-3-phenyl-3H-indolium 

Relevant academic research and scientific papers

Oxidation of Nonactivated Anilines to Generate N-Aryl Nitrenoids

A low-temperature, protecting-group-free oxidation of 2-substituted anilines has been developed to generate an electrophilic N-aryl nitrenoid intermediate that can engage in C-NAr bond formation to construct functionalized N-heterocycles. The exposure of 2-substituted anilines to PIFA and trifluoroacetic acid or 10 mol percent Sc(OTf)3 triggers nitrenoid formation, followed by productive and selective C-NAr and C-C bond formation to yield spirocyclic- or bicyclic 3H-indoles or benzazepinones. Our experiments demonstrate the breadth of these oxidative processes, uncover underlying fundamental elements that control selectivity, and demonstrate how the distinct reactivity patterns embedded in N-aryl nitrenoid reactive intermediates can enable access to functionalized 3H-indoles or benzazepinones.

I(III)-catalyzed oxidative cyclization - Migration tandem reactions of unactivated anilines

An I(III)-catalyzed oxidative cyclization-migration tandem reaction using Selectfluor as the oxidant was developed that converts unactivated anilines into 3H-indoles is reported herein. The reaction requires as little as 1 mol % of the iodocatalyst and is mild, tolerating pyridine and thiophene functional groups, and the dependence of the diastereoselectivity of the process on the identity of the iodoarene or iodoalkane precatalyst suggests that the catalyst is present for the stereochemical determining C-N bond forming step.

Substrate-controlled Rh(II)-catalyzed single-electron-transfer (SET): Divergent synthesis of fused indoles

Rh(ii)-catalyzed diversified ring expansions controlled by single-electron-transfer (SET) have been disclosed in this communication, producing a series of indole-fused azetidines and 1H-carbazoles or related derivatives in moderate to good yields via Rh2III,II nitrene radical intermediates. The direction of ring expansion branches according to different ring sizes of methylenecycloalkanes.

Promoting reductive tandem reactions of nitrostyrenes with Mo(CO)6 and a palladium catalyst to produce 3 h -indoles

The combination of Mo(CO)6 and 10 mol % of palladium acetate catalyzes the transformation of 2-nitroarenes to 3H-indoles through a tandem cyclization-[1,2] shift reaction of in situ generated nitrosoarenes. Mo(CO)6 appears to have dual roles in this transformation: generate CO and promote C-N bond formation to increase the yield of the N-heterocycle product.

General method for functionalized polyaryl synthesis via aryne intermediates

A method for base-promoted arylation of arenes and heterocycles by aryl halides and aryl triflates is described. Additionally, in situ electrophilic trapping of ArLi intermediates generated in the reaction of benzyne with deprotonated arenes or heterocycles has been developed, providing rapid and easy access to a wide range of highly functionalized polyaryls. Base-promoted arylation methodology complements transition-metal-catalyzed direct arylation and allows access to structures that are not easily accessible via other direct arylation methods. The reactions are highly functional-group tolerant, with alkene, ether, dimethylamino, trifluoromethyl, ester, cyano, halide, hydroxyl, and silyl functionalities compatible with reaction conditions.

On the reactivity of some 2-methyleneindolines with β-nitroenamines, α-nitroalkenes, and 1,2-diaza-1,3-butadienes

A study of the behaviour of some electron-rich 2-methyleneindolines (1-3) with different electron-poor reagents (formation of new carbon-carbon and nitrogen-carbon bonds) has furnished interesting results from both synthetic and the mechanistic viewpoints

Synthesis of a new series of indolinic aminoxyls. Reaction of indoles, 2-phenylbenzothiazole, 2-phenylbenzoxazole and 2-phenyl1,2-dihydro-4H-3,1-benzoxazin-4-one with organolithium reagents

2-Alkyl-2-phenyl-3,3-dimethylindolines. obtained by 1,2 organolithium addition to 2-phenyl-3,3-dimethyl-3H-indole, are converted into a new series of aminoxyls by oxidation with m-chloroperoxybenzoic acid. Attempts to synthesise, in a similar way suitable precursors such as 1,2-dihydro-2-phenyl-2-alkylbenzothiazole, 1,2-dihydro-2-phenyl-2-alkylbenzoxazole and 1,2-dihydro-2-phenyl-2-alkyl-4H-3,1-benzoxazin-4-one for other new aminoxyls failed. In fact, 2-phenylbenzothiazole, 2-phenylbenzoxazole and 2-phenyl-4H-3,1-benzoxazin-4-one react with organolithium reagents affording products deriving from ring opening. Crystal structures of 2,3-dimethyl-3-phenyl-3H-indole and bis(2-triphenylmetriylaminophenyl) disulfide are also described.