91897-61-9

Upstream product

• 196191-35-2 2-(6-Bromo-2,3-dimethoxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-N-(2,2-bis(phenylsulfanyl)ethenyl)acetamide 
• 196191-41-0 14-Benzenesulfinyl-3,4,11,12-tetramethoxy-8,9,14,14a-tetrahydro-5H-benzo[4,5]azepino[2,1-a]isoquinolin-6-one 
• 196191-39-6 5,6,8,9,14,14a-Hexahydro-3,4,11,12-tetramethoxy-14-phenylsulfanylisoquino[1,2-b][3]benzazepin-6-one 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 91897-62-0 5,6,8,9,14,14a-Hexahydro-14-hydroxy-3,4,11,12-tetramethoxyisoquino[1,2-b][3]benzazepin-6-one 
• 154535-11-2 5,6-dimethoxy-2-(3,4-dimethoxyphenyl)-3-oxo-1,2,3,4-tetrahydroisoquinolin-1-carboxylic acid 
• 196191-43-2 14-Trifluoroacetoxy-5,6,8,9,14,14a-hexahydro-3,4,11,12-tetramethoxyisoquino[1,2-b][3]benzazepin-6-one 
• 1027972-28-6 1,4-Dihydro-5,6-dimethoxy-2-[2-(3,4-dimethoxyphenyl)ethyl]-1-[(phenylsulfanyl)methyl]isoquinolin-3(2H)-one 
• 1026853-30-4 (2,2-Bis-phenylsulfanyl-vinyl)-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine 

Relevant academic research and scientific papers

Sulfur-controlled 6-exo aryl radical cyclisation of N-ethenyl-2-(2-bromophenyl)acetamides: Synthesis of (±)-tetrahydropalmatine and saulatine

Bu3SnH-mediated aryl radical cyclisation of 2-(2-bromophenyl)-N-[2,2-bis(phenylsulfanyl)ethenyl]-acetamide 7 takes place in a 6-exo-trig manner to give the isoquinolinone 9. The method has been applied to the synthesis of (±)-tetrahydropalmatine 16 and saulatine 24.

Synthesis of saulatine

A study directed toward the synthesis of saulatine (5,8,9,14a-tetrahydro- 3,4,11,12-tetramethoxy-isoquino[1,2-b]benzazepine-6,14-dione) is described. The successful synthetic route consists of three steps starting with 3,4- dimethoxyphenethylamine and 2-bromo-(3,4-dimethoxy-2- ethoxycarbomethylphenyl)-acetate. It was found that the methoxy moieties present on the aromatic rings prohibit the use of the intramolecular Friedel- Crafts reaction with a Lewis acid catalyst for ring construction because of their demethylation tendency under the reaction conditions.