27993-70-0

Usage

Uses

Used in Organic Synthesis:
2-Methoxyphenylglyoxal hydrate is utilized as a reagent in organic synthesis for the preparation of a wide array of heterocycles and functionalized organic molecules. Its unique structure allows for the creation of complex organic compounds that are essential in various chemical applications.
Used in Pharmaceutical Development:
2-METHOXYPHENYLGLYOXAL HYDRATE has been studied for its potential role in the development of pharmaceuticals, indicating its possible use as a key intermediate in the synthesis of new drug molecules. Its reactivity and functional groups make it a promising candidate for medicinal chemistry.
Used in Fluorescent Dyes and Materials:
2-Methoxyphenylglyoxal hydrate also serves as a precursor in the preparation of fluorescent dyes and materials. Its properties contribute to the development of compounds that have applications in areas such as bioimaging, diagnostics, and other fields where fluorescent markers are required.
Used in Material Science:
In the field of material science, 2-Methoxyphenylglyoxal hydrate is employed for its ability to contribute to the synthesis of new materials with specific properties. Its versatility in forming different types of chemical bonds makes it valuable in creating materials with tailored characteristics for specialized uses.

InChI:InChI=1/C9H8O3/c1-12-9-5-3-2-4-7(9)8(11)6-10/h2-6H,1H3

Upstream product

• 579-74-8 2-Methoxyacetophenone 
• 612-15-7 o-methoxystyrene 
• 135-02-4 ortho-anisaldehyde 
• 1374568-28-1 2,2-diiodo-1-(2-methoxyphenyl)ethanone 
• 1374568-05-4 2,2-diiodo-1-(2-methoxyphenyl)ethanol 

Downstream Products

• 122479-27-0 6-Chloro-2-(2-methoxy-phenyl)-imidazo[1,2-b]pyridazin-3-ol 
• 121041-15-4 3-methoxy-6-(3'-methoxybenzylthio)-2-(2''-methoxyphenyl)imidazo<1,2-b>pyridazine 
• 121246-99-9 6-chloro-3-methoxy-2-(2'-methoxyphenyl)imidazo<1,2-b>pyridazine 
• 111628-57-0 5-(2-methoxyphenyl)-3-(methylthio)-1,2,4-triazine 
• 1244783-59-2 C₃₀H₃₉N₃O₇ 
• 27993-82-4 2-(2'-methoxyphenyl)quinoxaline 
• 1268129-61-8 1-(2-methoxyphenyl)-2-(pyrrolidin-1-yl)ethane-1,2-dione 
• 1127405-05-3 1-(2-methoxyphenyl)-2-morpholinoethane-1,2-dione 
• 251933-26-3 2-(2-methoxyphenyl)pyrazine 
• 912763-39-4 C₁₁H₁₀N₂O₂ 
• 107943-61-3 1-(2-hydroxyphenyl)-2-(2-methoxyphenyl)ethane-1,2-dione 

Relevant academic research and scientific papers

C?H Methylation of Iminoamido Heterocycles with Sulfur Ylides**

The direct methylation of N-heterocycles is an important transformation for the advancement of pharmaceuticals, agrochemicals, functional materials, and other chemical entities. Herein, the unprecedented C(sp2)-H methylation of iminoamido heterocycles as nucleoside base analogues is described. Notably, trimethylsulfoxonium salt was employed as a methylating agent under aqueous conditions. A wide substrate scope and excellent level of functional-group tolerance were attained. Moreover, this method can be readily applied to the site-selective methylation of azauracil nucleosides. The feasibility of gram-scale reactions and various transformations of the products highlight the synthetic potential of the developed method. Combined deuterium-labeling experiments aided the elucidation of a plausible reaction mechanism.

Visible-light assisted one-pot preparation of aryl glyoxals from acetoarylones via in-situ arylacyl bromides formation: Selenium-free approach to acetoarylones oxidation

A novel visible-light (blue LEDs: hν?=?425?±?15?nm) photocatalyzed one-pot method for the synthesis of electronically diverse aryl glyoxals in good to excellent yields from acetoarylones and green regents such as air, vitamin C and dioxane dibromide has been described. In addition, an application of the current methodology has been demonstrated for the oxidation of monoamine oxidase-B inhibitors, i.e., 1-(4-((4-fluorobenzyl)oxy)phenyl)ethanone and 1-(3-((4-chlorobenzyl)oxy)phenyl)ethanone. This finding may serves as a valuable alternative to the traditional acetoarylones oxidation reactions conducted using selenium dioxide a harmful and unselective reagent known to simultaneously oxidize allylic, benzylic, [sbnd]CH3and so on.

Synthesis of 2-acyl-benzo[1,3-d]selenazoles via domino oxidative cyclization of methyl ketones with bis(2-aminophenyl) diselenide

A general, practical and simple one-pot synthesis of 2-acyl-benzo[1,3-d]selenazoles was developed by reacting a wide range of 2-arylethane-1,2-diones, generated in situ from commercially available aryl methyl ketones, with bis(2-aminophenyl) diselenide, promoted by Na2S2O5 in DMSO at 100 °C. Comparatively, the reactions were conducted under conventional heating and microwave irradiation. The use of focused microwave irradiation drastically decreased the reaction time from 48 to 2 h with a gain in the reaction yield for most cases. Still, 2-phenylacyl-benzo[1,3-d]selenazole was elected to react with sodium borohydride and butylmagnesium bromide, giving the respective secondary and tertiary alcohols under mild reaction conditions.

Iodine-mediated oxidative annulation for one-pot synthesis of pyrazines and quinoxalines using a multipathway coupled domino strategy

An efficient iodine-mediated oxidative annulation of aryl acetylenes-arylethenes-aromatic ketones with 1,2-diamines for the synthesis of pyrazines and regioselective synthesis of quinoxalines is presented. A multipathway coupled domino approach has been developed for the one-pot synthesis of 1,4-diazines with high functional group compatibility.

Metal-free oxidative amidation of 2-oxoaldehydes: A facile access to α-ketoamides

A novel and efficient method for the synthesis of α-ketoamides, employing a dimethyl sulfoxide (DMSO)-promoted oxidative amidation reaction between 2-oxoaldehydes and amines under metal-free conditions is presented. Furthermore, mechanistic studies supported an iminium ion-based intermediate as a central feature of reaction wherein C1-oxygen atom of α-ketoamides is finally derived from DMSO.

PYRIDOPYRAZINES AS ANTICANCER AGENTS

The present invention relates to pyridopyrazine derivatives and solvates, hydrates and pharmaceutically acceptable salts thereof, the use of them in the prevention and/or the treatment of cancer diseases, as well as pharmaceutical compositions containing at least one of them as pharmaceutically active agent(s) together with pharmaceutically acceptable carrier, excipient and/or diluents, especially for the prevention and/or treatment of cancer diseases.˙

Unexplored reactivity of 2-oxoaldehydes towards Pictet-Spengler conditions: Concise approach to β-carboline based marine natural products

Novel reactions under Pictet-Spengler conditions between tryptophan methyl ester/tryptamine and 2-oxoaldehydes have been developed and successfully utilized for the total synthesis of Merinacarboline (A and B), Eudistomin Y1, Pityriacitrin B, Pityriacitrin, Fascaplysin and analogues.

Quinoxaline derivatives: Novel and selective butyrylcholinesterase inhibitors

Alzheimer's disease (AD) is a progressive brain disorder which occurs due to lower levels of acetylcholine (ACh) neurotransmitters, and results in a gradual decline in memory and other cognitive processes. Acetycholinesterase (AChE) and butyrylcholinesterase (BChE) are considered to be primary regulators of the ACh levels in the brain. Evidence shows that AChE activity decreases in AD, while activity of BChE does not change or even elevate in advanced AD, which suggests a key involvement of BChE in ACh hydrolysis during AD symptoms. Therefore, inhibiting the activity of BChE may be an effective way to control AD associated disorders. In this regard, a series of quinoxaline derivatives 1-17 was synthesized and biologically evaluated against cholinesterases (AChE and BChE) and as well as against achymotrypsin and urease. The compounds 1-17 were found to be selective inhibitors for BChE, as no activity was found against other enzymes. Among the series, compounds 6 (IC50 = 7.7 ± 1.0μM) and 7 (IC50 = 9.7 ± 0.9 μM) were found to be the most active inhibitors against BChE. Their IC50 values are comparable to the standard, galantamine (IC50 = 6.6 ± 0.38 μM). Their considerable BChE inhibitory activity makes them selective candidates for the development of BChE inhibitors. Structure-activity relationship (SAR) of this new class of selective BChE inhibitors has been discussed.

Oxidative homologation of aldehydes to α-ketoaldehydes by using iodoform, o-iodoxybenzoic acid, and dimethyl sulfoxide

An efficient three-step synthetic route to α-ketoaldehydes starting from aryl aldehydes is reported. The aldehydes were treated with iPrMgCl and iodoform to obtain β-diiodoalcohols, which were then oxidized with o-iodoxybenzoic acid at room temperature to the corresponding β-diiodoketones. Subsequent reaction of the β-diiodoketone to the α-ketoaldehyde occurred under oxygen transfer from dimethyl sulfoxide. These sensitive products were in situ cyclized with o-phenylenediamine to form the stable monosubstituted quinoxalines, which could be characterized and isolated easily. α-Ketoaldehydes are a versatile, highly reactive moiety for the synthesis of heterocyclic compounds. We investigated the transformation of aldehydes into α-ketoaldehydes via β-diiodoketone intermediates and finally applied the procedure to the synthesis of peptidic substrates. Copyright

New heteroaromatic aminations on 5-aryl-1,2,4-triazines and 1,2,4,5-tetrazines by palladium catalysis

The efficient and original palladium-catalyzed amination of 5-Aryl-1,2,4-triazines and 1,2,4,5-tetrazines is reported. This Buchwald-Hartwig type reaction leads to the formation of aminated heterocycles via methylsulfur release. The reaction is optimized and a wide range of amines is used to determine the scope and limitations of this methodology.