20341-46-2

Upstream product

• 20341-14-4 N-[2-(1,3-benzodioxol-5-yl)ethyl]-2-(4-methoxyphenyl)acetamide 
• 802591-58-8 5-(4-methoxybenzyl)-7,8-dihydro[1,3]dioxolo[4,5-g]isoquinoline 
• 1384186-74-6 N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-2-(4-methoxyphenyl)-2-oxoacetamide 
• 13664-92-1 2,2-dibromo-1-(4-methoxyphenyl)ethanone 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 

Downstream Products

• 17656-61-0 (6,7-methylenedioxyisoquinolinyl)-(4'-methoxyphenyl)-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.

Synthesis of isoquinoline alkaloids via oxidative amidation-bischler- napieralski reaction

A straightforward synthesis of -keto amides by coupling primary amines with aryl dibromoethanones under oxidative amidation conditions has been developed. The -keto amides were then subjected to heterocyclodehydration reaction under Bischler-Napieralski conditions followed by aromatization with DBU provided 1-benzoyl isoquinolines in a two-stage process. Utilizing this methodology, isoquinoline alkaloids such as thalmicrinone, papavaraldine, and pulcheotine A were synthesized in excellent yields. Georg Thieme Verlag Stuttgart · New York.

A facile biogenetic synthesis of pulcheotine A

Starting from homopiperonylamine and 4-methoxyphenylacetic acid, a facile biogenetic route to naturally occurring pulcheotine A has been demonstrated via Pictet-Spengler cyclization and two different air oxidation processes. Georg Thieme Verlag Stuttgart.