522-57-6

Usage

Uses

Used in Pharmaceutical Industry:
(6,7-Dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to serve as a building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
(6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone is also used as a research tool in the field of organic chemistry. It can be employed to study the reactivity of different functional groups and to explore new synthetic pathways for the preparation of complex organic molecules.
Used in Material Science:
(6,7-Dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone may have potential applications in the development of new materials, such as organic semiconductors or optoelectronic devices, due to its electronic properties and the possibility of modifying its structure through chemical synthesis.
Used in Papaverine Production:
As an impurity in the production of Papaverine (P190500), a smooth muscle relaxant found in opium, (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone may play a role in the synthesis process or be a byproduct of the reaction. Its presence in the final product could have implications for the pharmacological activity or safety profile of Papaverine, and further research may be necessary to understand its effects.

InChI:InChI=1/C20H19NO5/c1-23-15-6-5-13(10-16(15)24-2)20(22)19-14-11-18(26-4)17(25-3)9-12(14)7-8-21-19/h5-11H,1-4H3

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 58-74-2 Papaverine 
• 71-43-2 benzene 
• 6957-27-3 3,4-dihydropapaverine 
• 50299-95-1 2-benzoyl-1-cyano-6,7-dimethoxy-1,2-dihydroisoquinoline 
• 20345-69-1 3,4-dihydropapaveraldine 
• 482-76-8 papaverinol 
• 17366-51-7 (Z)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 3947-79-3 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-3,4-dihydroisoquinolinium iodide 
• 61-25-6 papaverine hydrochloride 
• 83511-44-8 1-(2'-amino-4',5'-dimethoxy-α-oxobenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 13074-31-2 Tetrahydropapaverine 
• 7446-08-4 selenium(IV) oxide 

Downstream Products

• 861521-80-4 1-(3,4-dimethoxy-phenyl)-1-(7-hydroxy-6-methoxy-[1]isoquinolyl)-ethanol 
• 6152-76-7 6,7-dimethoxy-2-methyl-1-veratroyl-isoquinolinium; iodide 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 93-07-2 Veratric acid 
• 58-74-2 Papaverine 
• 20323-72-2 (6,7-dimethoxyisoquinolin-1-yl)(4,5-dimethoxy-2-nitrophenyl)-methanone 
• 482-76-8 papaverinol 
• 13074-31-2 Tetrahydropapaverine 
• 17656-58-5 (6,7-dimethoxy-isoquinolin-1-yl)-(3,4-dimethoxy-phenyl)-methanone oxime 
• 58024-44-5 6,7-dimethoxy-1-(3',4'-dimethoxy-α-hydroxy-α-methylbenzyl)isoquinoline 
• 58024-46-7 (6,7-dimethoxyisoquinolin-1-yl)-(3,4-dimethoxyphenyl)phenylcarbinol 
• 91790-53-3 1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline 
• 855427-50-8 papaveraldine thiosemicarbazone 
• 61-25-6 papaverine hydrochloride 

Relevant academic research and scientific papers

Hypervalent iodine oxidation products of papaverine and its microbial metabolites

(Diacetoxyiodo)benzene (DAIB) oxidizes papaverine to papaveraldine (2) and to 1-hydroxymethyl-6,7-dimethoxyisoquinoline (3), whereas 3'-desmethylpapaverine and 6-dexmethylpapaverine are converted into novel products (4) and (5), respectively.

Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis

A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.

Preparation method of papaverine compounds

The invention relates to a preparation method of papaverine compounds. Specifically, the invention relates to a preparation method of a compound as shown in a formula II, and the preparation method comprises a step of reacting a compound as shown in a formula III in the presence of an oxidizing agent. The method is high in yield, mild in reaction condition and suitable for industrial production.

One-Pot Synthesis of Papaverine Hydrochloride and Identification of Impurities

Abstract: A one-pot synthesis of papaverine hydrochloride with 99.6% purity was performed using xylene as solvent for the entire process. The critical parameters of each step, as well as the impurities generated, were identified. The overall yield was improved to 63%. The proposed synthetic procedure is suitable for industrial production.

Development of Pd(OAc)2-catalyzed tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids

A catalytic tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine in a 76% yield demonstrates the versatility of this catalytic reaction.

Electrochemical benzylic oxidation of C-H bonds

Oxidized products have become increasingly valuable as building blocks for a wide variety of different processes and fine chemistry, especially in the benzylic position. We report herein a sustainable protocol for this transformation through C-H functionalization and is performed using electrochemistry as the main power source and tert-butyl hydroperoxide as the radical source for the C-H abstraction. The temperature conditions reported here do not increase above 50 °C and use an aqueous-based medium. A broad substrate scope is explored, along with bioactive molecules, to give comparable and increased product yields when compared to prior reported literature without the use of electrochemistry.

Metal- and radical-free aerobic oxidation of heteroaromatic methanes: An efficient synthesis of heteroaromatic aldehydes

A metal-free and radical-free synthesis of heteroaromatic aldehydes was developed through aerobic oxidation of methyl groups in an I2/DMSO/O2 catalytic system. Under the reaction conditions, various functional groups such as methoxy, aldehyde, ester, nitro, amide, and halo (F, Cl, Br) groups were well tolerated. The bioactive compounds like chlorchinaldin derivative and papaverine were also oxidized to the corresponding aldehydes and ketones. This reaction provided an efficient method for preparing the valuable heteroaromatic aldehydes.

Visible-Light-Mediated Direct Decarboxylative Acylation of Electron-Deficient Heteroarenes Using α-Ketoacids

Acylation of electron-deficient heteroaromatic compounds has been developed using visible light. α-Ketoacids have been used as an efficient source of acyl radicals under photoredox conditions. The in situ generated acyl radicals from α-ketoacids have been coupled to a wide variety of electron-deficient heteroaromatic compounds in a Minisci type reaction. This method would be attractive to access biologically attractive molecules.

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.

Iron Complex Catalyzed Selective C-H Bond Oxidation with Broad Substrate Scope

The use of a peroxidase-mimicking Fe complex has been reported on the basis of the biuret-modified TAML macrocyclic ligand framework (Fe-bTAML) as a catalyst to perform selective oxidation of unactivated 3° C-H bonds and activated 2° C-H bonds with low catalyst loading (1 mol %) and high product yield (excellent mass balance) under near-neutral conditions and broad substrate scope (18 substrates which includes arenes, heteroaromatics, and polar functional groups). Aliphatic C-H oxidation of 3° and 2° sites of complex substrates was achieved with predictable selectivity using steric, electronic, and stereoelectronic rules that govern site selectivity, which included oxidation of (+)-artemisinin to (+)-10β-hydroxyartemisinin. Mechanistic studies indicate FeV(O) to be the active oxidant during these reactions.