493-49-2

Usage

Uses

Used in Pharmaceutical Industry:
6,7-DIMETHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE is used as a potential drug candidate for neurological disorders due to its effects on the central nervous system. It is being studied for its potential to treat various neurological conditions, given its pharmacological properties.
Used in Pain Management:
6,7-DIMETHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE is used as an analgesic agent. Its potential to alleviate pain is being explored, which could make it a valuable addition to the arsenal of pain management therapies.
Note: Since the provided materials do not specify different applications in various industries or the exact reasons for the applications, the uses listed are based on the general information provided about the compound's potential pharmacological properties. Further research and development would be necessary to confirm these uses and identify additional applications.

InChI:InChI=1/C11H13NO3/c1-14-9-5-7-3-4-12-11(13)8(7)6-10(9)15-2/h5-6H,3-4H2,1-2H3,(H,12,13)

Upstream product

• 593-56-6 N-methoxylamine hydrochloride 
• 132589-62-9 2-(2,2-Dimethyl-propionyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid 
• 56-23-5 tetrachloromethane 
• 17889-63-3 N-<2-(3,4-Dimethoxyphenyl)ethyl>carbamidsaeureethylester 
• 10025-87-3 trichlorophosphate 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 2328-12-3 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride 
• 35690-71-2 [2-(3,4-dimethoxy-phenyl)-ethyl]-carbamic acid methyl ester 
• 16101-63-6 6,7-dimethoxyisoquinoline-1(2H)-one 
• 55171-61-4 2-bromo-4,5-dimethoxybenzoyl chloride 
• 6286-46-0 2-bromo-4,5-dimethoxybenzoic acid 
• 82463-75-0 2-bromo-4,5-dimethoxy-benzamide 
• 243637-11-8 6,7-dimethoxy-1-oxo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 127119-08-8 3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester 

Downstream Products

• 26665-00-9 5,6-dihydro-2,3,10,11-tetramethoxy-13-methyl-8H-dibenzoquinolizin-8-one 
• 866756-40-3 2-(2-bromobenzoyl)-6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one 
• 116578-22-4 2-[N-Methyl-N-(4-(thien-2-yl)-butyl)-3-amino-propyl]-6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline-hydrochloride 
• 103936-91-0 2-(3-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)propyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-1(2H)-one 
• 76201-90-6 6,7-dimethoxy-1-<(para-chloro)phenyl>-3,4-dihydroisoquinoline 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 61011-86-7 5,6-dihydro-2,3-dimethoxy-8H-isoquinol<1,2-b>quinazolin-8-one 

Relevant academic research and scientific papers

Solid-phase synthesis of isoquinolinones using Bischler-Napieralski cyclization

A traceless solid-phase synthetic approach to isoquinolinones is described here. This approach allows introducing both electron-donating as well as electron-withdrawing moieties on the benzene nuclei of isoquinolinones with high yields and purities. Isoquinolinone is a structural unit found in many natural products having various important biological activities. A traceless solid-phase synthetic approach has been developed to prepare isoquinolinone derivatives. This approach enables one to synthesize isoquinolinones having various moieties on benzene nuclei and also can produce derivatives with a proton on the amide nitrogen.

Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues

A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.

A versatile approach to 1-oxo-, 1-oxo-3,4-dihydro- and 1,3,4-trioxo isoquinoline alkaloids and first total synthesis of the dimeric 1-oxoisoquinoline alkaloids berbanine and berbidine

We have worked out a very short approach to 1-oxoisoquinoline alkaloids starting from readily available 2-bromobenzamides utilizing a 2-ethoxyvinylboronate as a C2 building block for introduction of the C-3,C-4 unit of the isoquinoline core. TF

Easy Access to 2,4-Disubstituted Cyclopentenones by a Gold(III)-Catalyzed A3-Coupling/Cyclization Cascade

An efficient and convenient synthesis of 2,4-disubstituted cyclopentenones has been achieved through a Au(III)-catalyzed isomerization-A3-coupling/cyclization cascade. A possible mechanism involving an initial Au(III)-catalyzed isomerization, A3-type coupling, and cyclization via an enol intermediate is postulated.

Catalyst-free cyclization of anthranils and cyclic amines: One-step synthesis of rutaecarpine

An efficient synthesis of a variety of quinazolinone derivatives via a direct cyclization reaction between commercially available anthranils and cyclic amines is described. The developed transformation proceeds with the merits of high step- and atom-efficiency, a broad substrate scope, and good to excellent yields, without additional catalysts, and offers a practical way for the preparation of rutaecarpine and its derivatives with structural diversity.

Light-Driven Intramolecular C?N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex

Reported herein is a visible-light-driven intramolecular C?N cross-coupling reaction under mild reaction conditions (metal- and photocatalyst-free, at room temperature) via a long-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism.

A g-C3N4-based heterogeneous photocatalyst for visible light mediated aerobic benzylic C-H oxygenations

A metal-free heterogeneous photocatalytic system has been developed for highly efficient benzylic C-H oxygenations using oxygen as an oxidant. This visible light mediated oxidation reaction utilizes graphitic carbon nitride (g-C3N4) as a recyclable, nontoxic and low cost photocatalyst. Mild reaction conditions allow for the generation of synthetically and biologically valued isochromannones, phthalides, isoquinolinones, isoindolinones and xanthones from readily accessible alkyl aromatic precursors in good yields. The heterogeneous nature of the g-C3N4 catalytic system enables easy recovery and recycling as well as the use in multiple runs without loss of activity. The synthetic utility of this "green" methodology was further demonstrated by applying in bioactive and drug valued target syntheses.

Metal-Free Thermal Activation of Molecular Oxygen Enabled Direct α-CH2-Oxygenation of Free Amines

Direct oxidation of α-CH2 group of free amines is hard to achieve due to the higher reactivity of amine moiety. Therefore, oxidation of amines involves the use of sophisticated metallic reagents/catalyst in the presence or absence of hazardous oxidants under sensitive reaction conditions. A novel method for direct C-H oxygenation of aliphatic amines through a metal-free activation of molecular oxygen has been developed. Both activated and unactivated free amines were oxygenated efficiently to provide a wide variety of amides (primary, secondary) and lactams under operationally simple conditions without the aid of metallic reagents and toxic oxidants. The method has been applied to the synthesis of highly functionalized amide-containing medicinal drugs, such as O-Me-alibendol and -buclosamide.

One-Pot N-Deprotection and Catalytic Intramolecular Asymmetric Reductive Amination for the Synthesis of Tetrahydroisoquinolines

A one-pot N-Boc deprotection and catalytic intramolecular reductive amination protocol for the preparation of enantiomerically pure tetrahydroisoquinoline alkaloids is described. The iodine-bridged dimeric iridium complexes displayed superb stereoselectivity to give tetrahydroisoquinolines, including several key pharmaceutical drug intermediates, in excellent yields under mild reaction conditions. Three additives played important roles in this reaction: Titanium(IV) isopropoxide and molecular iodine accelerated the transformation of the intermediate imine to the tetrahydroisoquinoline product; p-toluenesulfonic acid contributed to the stereocontrol.

Supported Gold Nanoparticles for Efficient α-Oxygenation of Secondary and Tertiary Amines into Amides

Although the α-oxygenation of amines is a highly attractive method for the synthesis of amides, efficient catalysts suited to a wide range of secondary and tertiary alkyl amines using O2as the terminal oxidant have no precedent. This report describes a novel, green α-oxygenation of a wide range of linear and cyclic secondary and tertiary amines mediated by gold nanoparticles supported on alumina (Au/Al2O3). The observed catalysis was truly heterogeneous, and the catalyst could be reused. The present α-oxygenation utilizes O2as the terminal oxidant and water as the oxygen atom source of amides. The method generates water as the only theoretical by-product, which highlights the environmentally benign nature of the present reaction. Additionally, the present α-oxygenation provides a convenient method for the synthesis of18O-labeled amides using H218O as the oxygen source.