412337-64-5

Upstream product

• 351155-99-2 N-(2-(3,4-dimethoxyphenyl)ethyl)-2-(2-nitrophenyl)acetamide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 4230-93-7 3,4-dimethoxynitrostyrene 
• 22751-23-1 (2-nitrophenyl)acetyl chloride 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 67-66-3 chloroform 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 493-49-2 6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one 
• 132872-58-3 (2-aminophenyl)(6,7-dimethoxyisoquinolin-1-yl)methanone 
• 1262335-18-1 (Z)-6,7-dimethoxy-2-carbethoxy-1-(2-nitrobenzylidene)-1,2,3,4-tetrahydroisoquinoline 
• 15443-94-4 (6,7-dimethoxyisoquinolin-1-yl)(2-nitrophenyl)methanone 

Relevant academic research and scientific papers

Copper(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to 3,4-dihydroisoquinolines using air (O2) as a clean oxidant

A mild, efficient and eco-friendly method for the oxidation of 1-Bn-DHIQs to 1-Bz-DHIQs without concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs is very important for the syntheses of 1-Bz-DHIQ alkaloids and analogues. In this article, we developed a novel Cu(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to the C-1 positions of various 1-Bn-DHIQs. It was observed that when 0.2 equiv. of Cu(OAc)2·2H2O was used as the catalyst, 3.0 equiv. of AcOH was used as the additive and air (O2) was used as a clean oxidant, various 1-Bn-DHIQs could be efficiently oxidized to corresponding 1-Bz-DHIQs at 25 °C in DMSO. Especially, almost no concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs was observed during the above reaction. In addition, this method was successfully applied in the first total synthesis of the alkaloid canelillinoxine.

Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.