471908-63-1

Upstream product

• 20341-12-2 N-(2-benzo[1,3]dioxol-5-ylethyl)-2-phenylacetamide 
• 92665-05-9 1-benzyl-6,7-methylenedioxy-3,4-dihydroisoquinoline 
• 402717-64-0 phenyl-[6-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-methanone 

Downstream Products

• 17656-50-7 [1,3]dioxolo[4,5-g]isoquinolin-5-yl-phenyl-methanol 
• 20353-85-9 1-benzoyl-6,7-methylenedioxyisoquinoline 

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.

Desulfonylation of N-sulfonyl tetrahydroisoquinoline derivatives by potassium fluoride on alumina under microwave irradiation: Selective synthesis of 3,4-dihydroisoquinolines and isoquinolines

In a solvent-free system, the microwave irradiation of mixtures of N-sulfonyl tetrahydroisoquinolines and 37% potassium fluoride supported on alumina selectively furnished 3,4-dihydroisoquinolines or isoquinolines, depending upon the reaction time.