370558-21-7

Upstream product

• 257630-75-4 N-benzyl-N-(2-iodo-4-methylphenyl)cinnamamide 
• 370558-37-5 N-(2-iodo-4-methylphenyl)-N-benzyl-(α-deuterio)cinnamide 
• 55836-65-2 methyl (α-deuterio)cinnamate 
• 21788-36-3 (Z)-methyl 2-bromo-3-phenylacrylate 
• 42198-68-5 α-deuteriocinnamic acid 
• 29289-13-2 2-iodo-4-methylaniline 
• 100-39-0 benzyl bromide 
• 102-92-1 Cinnamoyl chloride 
• 370558-13-7 N-(2-iodo-4-methylphenyl)cinnamamide 
• 99448-75-6 1-benzyl-5-methylindoline-2,3-dione 
• 608-05-9 5-methyl-indole-2,3-dione 

Downstream Products

• 370558-28-4 3-hydroxy-1,3-dibenzyl-5-methylindolin-2-one 

Relevant academic research and scientific papers

Candida antarctica lipase-B-catalyzed kinetic resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles

Candida antarctica (CAL-B) lipase-catalyzed resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles has been performed to obtain (R)-1,3-dialkyl-3-acetoxymethyl oxindoles with up to 99% ee and (S)-1,3-dialkyl-3-hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)-3-allyl-3-hydroxymethyl oxindole to (3S)-1′-benzyl-5-(iodomethyl)-4,5-dihydro-2H-spiro[furan-3,3′-indolin]-2′-one. The optically active 3-substituted-3-hydroxymethyl oxindoles and spiro-oxindoles are among the key synthons in the synthesis of potentially biologically active molecules.

Cathodic reduction of N-(2-iodophenyl)-N-alkylcinnamides: A novel sequential electrochemical radical cyclisation and hydroxylation

In recent years, intramolecular aryl radical cyclisation has emerged as a useful route for the synthesis of benzannulated heterocycles and carbocycles. The aryl radicals are generated in situ from aryl halides (iodides or bromides) with tributylstannyl hydride-AIBN, SmI2, Co(I) or under photochemical conditions. The present work envisages the generation of aryl radicals by cathodic reduction of the carbon-iodine bond of N-(2-iodophenyl)-N-alkylcinnamides and their intramolecular cyclisation. The cathodic reduction of N-(2-iodophenyl)-N-alkyl-cinnamides under deaerated conditions in DMF gave 1-alkyl-3-benzylindolin-2-ones regioselectively and in the presence of oxygen yielded surprisingly 1-alkyl-3-hydroxy-3-benzylindolin-2-ones. Both these products were formed by a 5-exo-trig process in good yields. A mechanism for the formation of the products has been proposed through the use of cyclic voltammetry, coulometry and controlled-potential electrolysis as well as deuterium labelling.