169902-67-4

Upstream product

• 169902-65-2 (2-Benzo[1,3]dioxol-5-yl-ethyl)-(2,2-bis-phenylsulfanyl-vinyl)-amine 
• 153823-24-6 Bis(phenylsulfanyl)acetaldehyde 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 169902-69-6 N-<2-(3,4-Methylenedioxyphenyl)ethyl>-N-<2,2-bis(phenylsulfanyl)ethenyl>-6-bromo-2,3-dimethoxybenzamide 

Downstream Products

• 169902-68-5 2,3-Dihydro-N-<2-(3,4-methylenedioxyphenyl)ethyl>-6,7-dimethoxy-3-<(phenylsulfinyl)methyl>-1H-isoindol-1-one 

Relevant academic research and scientific papers

Sulfur-controlled 5-exo selective aryl radical cyclisation of N-vinylic 2-bromobenzamides: Synthesis of lennoxamine and chilenine

Bu3SnH-mediated aryl radical cyclisation of N-[2,2-bis(phenylsulfanyl)ethenyl]-2-bromobenzamides 12a-d and 16 takes place in a 5-exo manner to give exclusively the isoindolones 15a-d and 17, respectively. The isoindolone 17 is converted into lennoxamine and a key intermediate 20 for the synthesis of chilenine.

Sulfur-directed 5-exo selective aryl radical cyclization onto enamide: A simple route to chilenine

Bu3SnH-mediated aryl radical cyclization of the N-(o-bromoaroyl)enamine 5 took place in a 5-exo-trig manner exclusively to give isoindolone 7, which was transformed into the key intermediate 11 for the synthesis of isoindolobenzazepine alkaloid chilenine (2).