80688-36-4

Upstream product

• 2633-50-3 2-bromo-1-(3,4-dimethylphenyl)ethanone 
• 3637-01-2 3,4-dimethylacetophenone 
• 95-47-6 o-xylene 
• 109300-45-0 2,2-Dichloro-1-(3,4-dimethyl-phenyl)-ethanone 

Downstream Products

• 80120-32-7 ethyl 2-(3,4-dimethylphenyl)-2-oxoacetate 
• 619-04-5 3,4-dimethylbenzoic acid 
• 59411-15-3 1-(3,4-dimethylphenyl)-2-phenylethane-1,2-dione 
• 1267971-97-0 1-(3,4-dimethylphenyl)-2-(piperidin-1-yl)ethane-1,2-dione 
• 128863-46-7 3-methoxy-6-(2'-methoxyphenoxy)-2-(3,4-dimethylphenyl)imidazo<1,2-b>pyridazine 
• 121247-04-9 6-chloro-2-(3',4'-dimethylphenyl)-3-methoxyimidazo<1,2-b>pyridazine 

Relevant academic research and scientific papers

Direct preparation of indole hemiaminals through organocatalytic nucleophilic addition of indole to aldehydes

Hemiaminals are common in natural products as well as bioactive compounds. Hemiaminals with an indole moiety are particularly attractive due to the significant bioactivity of indoles. Herein, we reported an efficient organocatalyzed indole N-1 nucleophilic addition of α-oxoaldehydes to deliver various indole hemiaminals in good yields (up to 92percent) and excellent regioselectivities with DABCO or triethylamine as the catalyst. The method is characterized by mild reaction conditions, widely available reagents, and general substrate scope, and it is also applicable to late-stage transformations without affecting the hemiaminal group. In addition, we carried out this reaction in an enantioselective fashion in good yields and high ee values with two general substrates.

Asymmetric Conjugate Addition of α-Cyanoketones to Benzoyl Acrylonitrile Derivatives Using a Diaminomethylenemalononitrile Organocatalyst

A diaminomethylenemalononitrile (DMM) organocatalyst was used to efficiently promote asymmetric conjugate addition of various α-cyanoketones to benzoyl acrylonitrile derivatives. The corresponding 1,5-dicarbonyl compounds containing vicinal tertiary and quaternary stereogenic centers are versatile synthetic intermediates and were obtained in good yields and with excellent enantioselectivities (up to 96% ee). The present study describes the first successful examples of asymmetric conjugate addition reactions of α-cyanoketones with benzoyl acrylonitriles. In addition, the DMM organocatalyst can be recovered and reused up to five times without significant loss of either catalytic activity or enantioselectivity.

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.

Iridium-Catalyzed Asymmetric Hydrogenation of Unsaturated Piperazin-2-ones

Two different iridium catalyst systems, generated from the ruthenocene-based phosphine-oxazoline ligand tBu-mono-RuPHOX or the diphosphine ligand BINAP, were developed for the asymmetric hydrogenation of 5,6-dihydropyrazin-2(1H)-ones, affording chiral piperazin-2-ones in good yields and with moderate to good ees. Different catalytic behaviors for the hydrogenation of these types of substrate were observed with these two catalyst systems. Our tBu-mono-RuPHOX ligand, which bears a ruthenocene scaffold with planar chirality, was found to be the best ligand for the [Ir(L)(COD)]BArF catalyst system, affording the desired products with up to 94% ee. (Figure presented.).

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.

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.

Oxidation of aryl and heteroaryl methyl ketone to aryl and heteroarylglyoxals by using CuCl2-DMSO

The oxidation of aryl methyl ketone and heteroaryl methyl ketone to arylglyoxals and heteroaryl glyoxal respectively has been carried out by using the cheap and easily available, non toxic, Lewis acid CuCl2 in DMSO solvent at 70-80°C within 1-2 hr. The reaction can be performed in air without loss of variety of oxidisable fuctional group like phenolic OH, hetroaryl ring, aryl substituted methyl, halo, nitro group, etc.

3-ALKYLIDENEHYDRAZINO SUBSTITUTED HETEROARYL COMPOUNDS AS THROMBOPOIETIN RECEPTOR ACTIVATORS

A compound represented by the formula (1): wherein A is a nitrogen atom or CR4, B is an oxygen atom, a sulfur atom or NR9 (provided that when A is a nitrogen atom, B is not NH), R1 is a C2-14; aryl group, L1 is a bond, CR10R11, an oxygen atom, a sulfur atom or NR12, X is OR13, SR13 or NR14NR15, R2 is a hydrogen atom, a formyl group, a C1-10; alkyl group or the like, L2 is a bond or the like, L3 is a bond, CR17R18, an oxygen atom, a sulfur atom or NR19, L4 is a bond, CR20R21, an oxygen atom, a sulfur atom or NR22, Y is an oxygen atom, a sulfur atom or NR23, and R3 is a C2-14; aryl group, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.

Benzo[1,8]naphthyridine derivatives, their preparation and compositions containing them

New benzo[b][1,8]naphthyridine derivatives of general formula (I), in which R1 is a hydrogen atom or a hydroxyl or alkyl radical, R2 is a hydrogen atom or an alkyl, fluoroalkyl, cycloalkyl (3 to 6 C), alkyloxy or alkylamino radical, R3 is a phenyl or phenylalkyl radical substituted with one or more halogen atoms or alkyl, cycloalkyl (3 to 6 C), alkyloxy, cyano, amino, alkylamino, dialkylamino, alkyloxyalkyl, hydroxyalkyl, hydroxyalkyloxy, methylenedioxy, aminoalkyl, alkylaminoalkyl or dialkylaminoalkyl radicals, or R3 is a heterocyclic radical, and R4 is a hydrogen atom or a fluorine atom, the alkyl radicals (1 to 4 C) being linear or branched, their salts, their preparation and compositions containing them. These new products are useful as antimicrobials, or in the treatment of AIDS. STR1

A New Synthetic Route to Aromatic Gyloxals

Dichloroacylation of toluene, o- and m- xylenes, chloro- and bromo-benzenes and m-chlorotoluene under Friedel-Crafts conditions leads to the corresponding chloroketones (Ia-f) which on controlled hydrolysis afford the glyoxals (IIa-f) respectively.