113575-52-3

Upstream product

• 113557-31-6 N-(3,4-dimethoxybenzyl)-N-(2,3-dimethoxyphenethyl)-α-(methylsulfinyl)acetamide 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 47355-66-8 N-(2,3-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethan-1-amine 
• 113557-30-5 N-(3,4-dimethoxybenzyl)-N-(2,3-dimethoxyphenethyl)-α-(methylthio)acetamide 
• 109806-78-2 N-(2,3-dimethoxybenzylidene)-2-(3,4-dimethoxyphenyl)ethanamine 

Downstream Products

• 26067-60-7 2,3,9,10-tetramethoxy-5,8-dihydro-6H-isoquinolino[3,2-α]isoquinoline 
• 2934-97-6 (+/-)-tetrahydropalmatine 
• 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).