113557-37-2

Upstream product

• 63375-81-5 2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 113557-33-8 2-bromo-4,5-dimethoxy-N-(2,3-dimethoxybenzyl)phenethylamine 

Downstream Products

• 264625-26-5 2-(2-bromo-4,5-dimethoxyphenethyl)-4-ethyl-7,8-dimethoxy-4-methylthio-1,2,3,4-tetrahydroisoquinolin-3-one 
• 26067-60-7 2,3,9,10-tetramethoxy-5,8-dihydro-6H-isoquinolino[3,2-α]isoquinoline 
• 264625-27-6 7,8-dimethoxy-2-(3,4-dimethoxyphenethyl)-4-methyl-1,2,3,4-tetrahydroisoquinolin-3-one 
• 264625-28-7 4-ethyl-7,8-dimethoxy-2-(3,4-dimethoxyphenethyl)-1,2,3,4-tetrahydroisoquinolin-3-one 
• 2934-97-6 (+/-)-tetrahydropalmatine 
• 264625-24-3 2-(2-bromo-4,5-dimethoxyphenethyl)-7,8-dimethoxy-4-methyl-4-methylthio-1,2,3,4-tetrahydroisoquinolin-3-one 
• 113557-41-8 7,8-dimethoxy-2-(3,4-dimethoxyphenethyl)-1,2,3,4-tetrahydroisoquinolin-3-one 

Relevant academic research and scientific papers

Convenient synthesis of 2,3,9,10-tetraoxygenated protoberberine alkaloids and their 13-methyl alkaloids

New and convenient synthesis of 2,3,9,10-tetraoxygenated protoberberine alkaloids and their 13-methyl alkaloids through the same intermediates was developed. Acylation of the brominated benzylphenethylamine (13) with α- chloro-α-(methylthio)acetyl chloride, followed by cyclization with stannic chloride, furnished the key intermediates 4-methylthio-3- phenethylisoquinolin-3-ones (14), which were methylated to provide their methyl derivatives (17). Both isoquinolin-3-ones (14, 17) were easily transformed into protoberberine alkaloids (16) and their 13-methyl alkaloids (21) in good yield.

A NEW AND CONVENIENT SYNTHESIS OF PROTOBERBERINE ALKALOIDS: (+/-)-TETRAHYDROPALMATINE, (+/-)-SINACTINE, (+/-)-CANADINE AND-)-STYLOPINE

2,3,9,10-Tetraoxygenated protoberberine alkaloids (14) were efficiently synthesized from the readily available benzaldehyde (2 or 10) via the benzylphenethylamines (11) and 2-phenethylisoquinolin-3-ones (12 or 13).