62236-19-5

Upstream product

• 576-15-8 N-acetylindole 
• 71-43-2 benzene 
• 1504-16-1 3-phenyl-1H-indole 
• 3963-62-0 2,2-Diphenylethylamine 
• 1181068-31-4 N-(2,2-diphenylethyl)picolinamide 
• 1352819-02-3 (3-phenylindolin-1-yl)(pyridin-2-yl)methanone 
• 182165-50-0 1-acetyl-3-phenylindoline 

Downstream Products

• 1439858-91-9 1-(2-methylbut-3-en-2-yl)-3-phenyl-1H-indole 
• 1439859-60-5 1-(2-methylbut-3-en-2-yl)-3-phenyl-1H-indoline 
• 1504-16-1 3-phenyl-1H-indole 
• 727416-65-1 3-phenyl-1-(toluene-4-sulfonyl)-1H-indole 
• 119199-38-1 3-Phenyl-2,3-dihydro-indole-1-carboxylic acid ((1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide 
• 119199-53-0 3-Phenyl-2,3-dihydro-indole-1-carbonyl chloride 

Relevant academic research and scientific papers

Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization

The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and experimental results of the biotransformation. This methodology represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.

Sustainable Radical Cascades to Synthesize Difluoroalkylated Pyrrolo[1,2-a]indoles

We disclose herein a photocatalytic difluoroalkylation and cyclization cascade reaction of N-(but-2-enoyl)indoles with broad substrate scopes in up to 90% isolated yield. This method provides sustainable and efficient access to synthesize difluoroalkylated pyrrolo[1,2-a]indoles with a quaternary carbon center under mild conditions.

The cooperative FeCl3/DDQ system for the regioselective synthesis of 3-arylindoles from β-monosubstituted 2-alkenylanilines

A highly regioselective synthesis of 3-arylindoles by using the cooperative FeCl3/DDQ system has been developed. This new protocol represents an attractive route for the synthesis of 3-arylindoles from readily accessible non-indole precursors, β-aryl-substituted 2-styrylanilines, using an inexpensive catalyst and oxidant. Noteworthy is the unique synergetic and synergistic effect of FeCl3 and DDQ on the 1,2-aryl migratory process.

Synthesis of indolines by copper-mediated intramolecular aromatic C-H amination

A Cu(OAc)2-mediated intramolecular aromatic C-H amination proceeds with the aid of a picolinamide-type bidentate coordination group to deliver the corresponding indolines in good yields. The reaction occurs smoothly even under noble-metal-free conditions, and in some cases the use of an MnO2 terminal oxidant renders the process catalytic in Cu. The mild oxidation aptitude of Cu(OAc)2 and/or MnO2 accommodates the formation of electron-rich thiophene-and indole-fused indoline analogues. The Cu-based system can provide an effective approach to various indolines of potent interest in pharmaceutical and medicinal chemistry.

Palladium-catalyzed synthesis of N-tert-prenylindoles

Palladium-catalyzed N-tert-prenylations of indoles, tricarbonylchromium- activated indoles, and indolines that occur in high yields (up to 94%) with high tert-prenyl-to-n-prenyl selectivity (up to 12:1) are reported.

Heterocycle synthesis via direct C-H/N-H coupling

A method for five- and six-membered heterocycle formation by palladium-catalyzed C-H/N-H coupling is presented. The method employs a picolinamide directing group, PhI(OAc)2 oxidant, and toluene solvent at 80-120 °C. Cyclization is effective for sp2 as well as aliphatic and benzylic sp3 C-H bonds.

Process for producing indoline compounds and intermediates for the production of the same

This invention concerns a method for the production of a 3-arylindoline compound represented by the general formula STR1

Indoline compound and 5-HT3 receptor antagonist containing the same as active ingredient

Indoline compounds represented by the general formula: STR1 wherein R1 represents the group STR2 R2 represents a phenyl group which may be substituted or an aromatic heterocyclic group, and R3 represents hydrogen, a halogen, or a lower alkyl group, hydroxyl group, lower alkoxy group, carbamoyl group or lower alkoxycarbonyl group, and physiologically acceptable salts thereof, and their solvates, as well as 5-HT3 receptor antagonists containing them as effective components. The indoline compounds of the invention have stronger antagonism against intestinal 5-HT3 receptors than known 5-HT3 receptor antagonists and also have excellent sustained action, making them useful as prophylactic or therapeutic agents against vomiting or irritancy induced by chemotherapy or radiation, irritable bowel syndrome, diarrhea, and the like.