122101-01-3

Upstream product

• 100-39-0 benzyl bromide 
• 118670-85-2 (2E)-N-(2-iodophenyl)-3-phenylprop-2-enamide 
• 615-43-0 2-iodophenylamine 
• 102-92-1 Cinnamoyl chloride 
• 105041-05-2 3-phenyl-2-propenoyl bromide 
• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 36208-62-5 1,3-dibenzyl-1,3-dihydroindol-2-one 
• 35887-49-1 1,3-dibenzyl-3-hydroxy-1,3-dihydro-2H-indol-2-one 
• 30015-72-6 2,4-dibenzyl-2H-benzo[b][1,4]thiazin-3(4H)-one 

Relevant academic research and scientific papers

Copper-catalyzed highly selective synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[: B] thiazinones from 2-iodophenylcinnamamides and potassium sulfide

An efficient and practical procedure for the synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[b]thiazinones from easily available 2-iodophenylcinnamamides and potassium sulfide has been developed. In the presence of DBU, the reaction proceeds vi

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.

N-Benzyl-2′-iodocinnamanilide and N-benzyl-2′-iodo-4′-methyl-2-phenyl-cinnamanilide

The aromatic ring of the cinnamic moiety in N-benzyl-2′-iodocinnamanilide, C22H18INO, (I), and N-benzyl-2′-iodo-4′-methyl-2-phenylcinnamanilide, C29H24INO, (II), makes a dihedral angle with the iodophenyl ring o

SYNTHESIS OF OXINDOLES BY RADICAL CYCLISATION

Oxindoles are readily synthesised by intramolecular addition of aryl radicals to the α-position of α,β-unsaturated N-alkylamides.