99893-13-7

Upstream product

• 112632-97-0 2-Methoxy-2-phenyl-1-acetyl-2,3-dihydro-1H-indol-3-one 
• 591-50-4 iodobenzene 
• 16800-68-3 1-acetyl-2,3-dihydro-1H-indol-3-one 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 88-65-3 2-bromobenzoic-acid 
• 2835-06-5 phenylglycin 
• 84970-05-8 (2-carboxy-anilino)-phenyl-acetic acid 
• 84970-12-7 3-acetoxy-1-acetyl-2-phenyl-1H-indole 
• 66003-76-7 Diphenyliodonium triflate 
• 1483-73-4 diphenyliodonium bromide 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 6293-66-9 diphenyliodonium p-toluenesulfonate 
• 25365-71-3 2-phenyl-1H-indol-3-carboxaldehyde 

Downstream Products

• 1006692-46-1 1-acetyl-2-(3-methylbut-2-enyl)l-2-phenylindolin-3-one 
• 27005-52-3 2-(2-phenyl-1H-indol-3-yl)acetonitrile 
• 143466-28-8 1-Acetyl-2-(2,4-dimethoxy-phenyl)-2-phenyl-1,2-dihydro-indol-3-one 

Relevant academic research and scientific papers

Palladium-catalyzed direct C(sp3)-H arylation of indole-3-ones with aryl halides: A novel and efficient method for the synthesis of nucleophilic 2-monoarylated indole-3-ones

A novel and efficient method for the synthesis of nucleophilic 2-monoarylated indole-3-ones via palladium-catalyzed direct C(sp3)-H arylation of indole-3-ones with aryl halides has been developed. Various 2-monoarylated indole-3-ones were readily obtained with yields up to 95%. As a class of important nucleophilic intermediates, 2-monoarylated indole-3-ones can be used for the construction of C2-quaternary indolin-3-one skeletons.

Synthesis of 2-allyl-2,3-dihydro-1H-indol-3-ones using in situ Claisen rearrangement of 2,3-dihydro-1H-indol-3-ones with allyl alcohols

Treatment of 2,3-dihydro-1H-indol-3-ones with allyl alcohols in the presence of camphorsulfonic acid and magnesium sulfate at 130°C gave, via condensation and a Claisen rearrangement, 2-allyl-2,3-dihydro-1H-indol-3-ones in good yields. The stereochemistry of the products was determined by NOE experiments.

Palladium-catalyzed α-arylation of indolin-3-ones

A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)2 and PAd3 was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line.

Indoxyl-based umpolung strategy for the synthesis of unsymmetrical 3,3′-biindoles

3,3′-Bisindoles are known to be important structural motifs found in bioactive natural products, pharmaceuticals, and functional materials. Herein, a novel indoxyl-based approach was established for the synthesis of unsymmetrical 3,3′-biindoles from indoles and indoxyls. This approach generated moderate to excellent yields of the desired products (24 examples, up to 98% yield). The present method features broad substrate scope, operational simplicity, high atom economy, and utilization of non-toxic and inexpensive molecular iodine as catalyst. The applicability of this method has been demonstrated by the facile gram-scale synthesis.

Tert -Butoxide-Mediated Arylation of 1-Acetylindolin-3-ones with Diaryliodonium Salts

A procedure for the 2-arylations of indolinone derivatives with diaryliodonium salts mediated by potassium tert-butoxide is developed. Various monoarylated indolinone derivatives are readily obtained in 24-70% yield via this method. The alkylation of monoarylated indolinone derivatives with allyl bromide or benzyl bromide affords the corresponding 2,3-disubstituted products in 60% and 70% yield, respectively.

A convenient synthesis of 1,2-dihydro-3H-indol-3-ones and 1,2-dihydro-2H-indol-2-ones by Baeyer-Villiger oxidation

The Baeyer-Villiger rearrangement of substituted 1H-indole-3-carbaldehydes afforded the corresponding substituted 1,2-dihydro-3H-indol-3-ones. The influence of 3-carbonyl and 1-protecting groups has been examined. Reaction has been extended to 1H-indole-2-carbaldehydes and used for synthesis of 1-(phenylsulfonyl)-1H-indol-2-yl trifluoromethanesulfonate.

Oxidation of Indoles with Oxodiperoxomolybdenum (VI), MoO5*HMPA. Preparation of 2-Hydroxyindoxyl and Isatogen Derivatives

Oxidation of 1-acetylindoles 1 with (hexamethylphosphoramide)oxodiperoxomolybdenum(VI), MoO5*HMPA, in dry methylene chloride gave 1-acetyl-2-hydroxyindoxyls 4. 2-Phenylindole (8) was similarly treated with MoO5*HMPA to give a dimeric product 11, while oxi