22190-45-0

Upstream product

• 4876-02-2 N-(3,4-dimethoxyphenethyl)-phenyl acetamide 
• 160852-78-8 N-(3,4-dimethoxyphenethyl)-2-oxo-2-phenylacetamide 
• 13665-04-8 2,2-dibromoacetophenone 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 260552-68-9 (2-bromo-phenyl)-(6,7-dimethoxy-3,4-dihydro-[1]isoquinolyl)-ketone 
• 112970-37-3 2-acetyl-1-benzylidene-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline 
• 4876-00-0 1-benzyl-6,7-dimethoxy-3,4-dihydro-isoquinoline 

Downstream Products

• 120034-54-0 (1S,10bS)-8,9-Dimethoxy-1-phenyl-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinoline 
• 47145-36-8 (1S)-1-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 120142-62-3 (+)-(1S,αR)-1,2,3,4-tetrahydro-6,7-dimethoxy-α-phenyl-1-isoquinolinemethanol 
• 120142-61-2 (-)-(1R,αS)-1,2,3,4-tetrahydro-6,7-dimethoxy-α-phenyl-1-isoquinolinemethanol 
• 120142-65-6 erythro-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-α-phenyl-1-isoquinolinemethanol 
• 86970-95-8 threo-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-α-phenyl-1-isoquinolinemethanol 
• 120142-64-5 (-)-(1S,αR)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-α-phenyl-1-isoquinolinemethanol 
• 120142-63-4 (+)-(1R,αS)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-α-phenyl-1-isoquinolinemethanol 
• 120034-53-9 1,2,3,4-tetrahydro-6,7-dimethoxy-α-phenyl-2-<((R)-1-phenylethyl)carbamoyl>-1-isoquinolinemethanol 
• 120034-53-9 (1R,αS)-1,2,3,4-tetrahydro-6,7-dimethoxy-α-phenyl-2-<((R)-1-phenylethyl)carbamoyl>-1-isoquinolinemethanol 
• 120142-59-8 (1S,αR)-1,2,3,4-tetrahydro-6,7-dimethoxy-α-phenyl-2-<((R)-1-phenylethyl)carbamoyl>-1-isoquinolinemethanol 
• 20359-09-5 (6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)(phenyl)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.

Aryl radical cyclizations of 1-(2′-bromobenzyl)isoquinolines with AIBN-Bu3SnH: Formation of aporphines and indolo[2,1-a]isoquinolines

(matrix presented) Radical cyclization of alkoxy-substituted 1-(2′-bromobenzyl)-3,4-dihydroisoquinolines 1 with AIBN-Bu3SnH gave 6a,7-dehydroaporphines 2 preferentially. A steric repulsion between the respective alkoxy groups at the 7- and 3′-positions gave 5,6-dihydroindolo[2,1-a]isoquinolines 3 in a disfavored 5-endo cyclization mode. Radical cyclizations of the related substrates, such as 1-(2′-bromobenzoyl)isoquinolines or 1-(2′-bromo-α-hydroxybenzyl)isoquinolines, were also found to give the corresponding oxoaporphines or oxyaporphines.

Lead Tetraacetate Mediated Oxidation of the Enamides Derived from 1-Benzyl-3,4-dihydroisoquinolines

The products obtained from the lead tetraacetate (LTA) oxidation of N-acylbenzylidene isoquinoline enamides are a function of the type of carbonyl function in the enamide, the solvent,and the type of substitution on the benzylidene aromatic ring.The benzoyl enamides yield Z-β-acethoxy-substituted enamides.The ethoxycarbonyl enamides, containing electron-releasing substituents on the benzylidene ring, efficiently form oxazolones when oxidized with LTA in acetic acid.In the absence of electron-releasing substituents, ring opening occurs to form benzoin esters.When the same oxidation is conducted in benzene, the enamide double bond is converted into its diacetoxy derivative, which can undergo a variety of reactions.LTA oxidation of acetyl enamides results in cleavage of the acetyl group with ultimate formation of 1-benzoyl-3,4-dihydroisoquinolines and isoquinolines.Oxidation of the formyl enamide with LTA results in cleavage of the formyl group with formation of a variety of products.Most of these have an acetyl group in place of the original formyl and are the result of either cleavage of the benzylidene ring at the double bond, oxidation, and subsequent ring opening to a benzil or various other oxidative and rearrangement processes.

Oxidation of Imines by Selenium Dioxide

The oxidation of imines containing a α-methylene group by selenium dioxide is investigated.The products are shown to be α-imino carbonyl compounds by spectroscopic methods.The reactivity of various imines is discussed. - Keywords: Selenium Dioxide, Imines, α-Imino Carbonyl Compounds

Rearrangement of 1-(α-Hydroxybenzyl)-1,2,3,4-tetrahydroisoquinolines to 1-Phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines

When methoxy-substituted 1-(α-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinolines are heated in formic acid they rearrange initially to give 5-phenyl-2,3-dihydro-1H-3-benzazepines which, on further heating in formic acid, are reduced to 1-phenyl-2,3,4,5-tetrah