Month: November 2022

Gao, Xiang published the artcileDBU coupled ionic liquid-catalyzed efficient synthesis of quinazolinones from CO2 and 2-aminobenzonitriles under mild conditions, Name: 2-Aminobenzonitrile(Flakes or Chunks), the main research area is quinazolinone preparation organic base ionic liquid catalyst; aminobenzonitrile carbon dioxide cyclization diazabicycloundecene ionic liquid catalyst.

An efficient catalytic system of organic base-coupled ionic liquids (ILs) that could catalyze the synthesis of quinazolinones I (R1 = H, OMe, Cl, Br, R2 = H; R1 = H, R2 = Cl) via cyclization of 2-aminobenzonitriles with CO2 under mild conditions (e.g., 60°C, 0.1 MPa) was reported. It was found that 1,8-diazabicyclo[5.4.0]undec-7-ene coupled with 1-butyl-3-methylimidazole acetate ionic liquids, (DBU/[Bmim][OAc]), displayed excellent performance in catalyzing the reactions of CO2 with 2-aminobenzonitriles to give compounds I in high yields at atm. pressure. Moreover, the ILs had high stability and reusability, and could be reused at least five times without considerable decrease in catalytic activity. This protocol could also be conducted on a gram scale, and may have promising and practical applications in the production of quinazolinones.

RSC Advances published new progress about Aromatic nitriles Role: RCT (Reactant), RACT (Reactant or Reagent) (amino). 1885-29-6 belongs to class nitriles-buliding-blocks, name is 2-Aminobenzonitrile(Flakes or Chunks), and the molecular formula is C7H6N2, Name: 2-Aminobenzonitrile(Flakes or Chunks).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wang, Qi published the artcileEfficient Synthesis of Quinazolinones by Transition-Metal-Free Direct Aerobic Oxidative Cascade Annulation of Alcohols with o-Aminoarylnitriles, Synthetic Route of 1885-29-6, the main research area is quinazolinone preparation green chem; alc aryl nitrile amino aerobic oxidative cascade annulation; aerobic oxidation; alcohols; annulation; o-aminobenzonitriles; quinazolinones.

A mild and atom-economic method was developed for direct and efficient synthesis of quinazolinones I (R1 = H, 5-Cl, 6-Br, 7-CH3, etc.; R2 = C6H5, naphthalen-2-yl, thiophen-2-yl, etc.) through a transition-metal-free aerobic oxidative cascade annulation reaction of widely available o-aminoarylnitriles R32-H2NC6H3CN (R3 = H, 4-CH3, 5-Br, 6-Cl, etc.) and alcs. R2CH2OH. Air could be employed as an effective oxidant under mild conditions, generating water as the only byproduct. Possibly owing to the ”cesium effect”, the water-soluble base CsOH was found to be crucial in all key steps of the reaction mechanism. Because a wide range of substrates can be used to prepare substituted quinazolinones without contamination by transition-metal residues, this method may be of interest for application in pharmaceutical synthesis. Possible reaction paths were also proposed according to control reactions.

ChemSusChem published new progress about Aromatic nitriles Role: RCT (Reactant), RACT (Reactant or Reagent) (amino). 1885-29-6 belongs to class nitriles-buliding-blocks, name is 2-Aminobenzonitrile(Flakes or Chunks), and the molecular formula is C7H6N2, Synthetic Route of 1885-29-6.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sheng, Zhi-Zheng published the artcileAlcohol amine-catalyzed CO2 conversion for the synthesis of quinazoline-2,4-(1H,3H)-dione in water, Formula: C7H6N2, the main research area is quinazoline dione preparation green chem; aminobenzonitrile carbon dioxide cyclization diethanolamine catalyst.

The conversion of CO2 to high value-added chems. in water using environmentally friendly and cost-effective catalysts is a very significant topic. In this work, a green method for the conversion of CO2 catalyzed by alc. amines has been developed. Alc. amines showed considerable activating ability to CO2 in the cyclization with 2-aminobenzonitrile to quinazoline-2,4(1H,3H)-dione in water. Notably, when diethanolamine (DEA) was used as the catalyst, 94% yield of quinazoline-2,4-(1H,3H)-dione could be achieved. A plausible mechanism has been proposed based on the 1H NMR, FT-IR anal. and DFT calculation The excellent catalytic performance is attributed to the combined effect of both the secondary amine and hydroxyl groups on alc. amines with the assistance of water in the formation of carbamate. Water plays a bi-functional role of solvent and co-catalyst in this catalytic process. Catalysts can be easily recovered and reused five times without significant loss of activity.

RSC Advances published new progress about Aromatic nitriles Role: RCT (Reactant), RACT (Reactant or Reagent) (amino). 1885-29-6 belongs to class nitriles-buliding-blocks, name is 2-Aminobenzonitrile(Flakes or Chunks), and the molecular formula is C7H6N2, Formula: C7H6N2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kalaus, Hubert published the artcileA Kinetic Photometric Assay for the Quantification of the Open-Chain Content of Aldoses, Safety of 2-Aminobenzonitrile(Flakes or Chunks), the main research area is kinetic photometric quantification aldehyde selective conformation aldose aminobenzamidoxime; Aldehydes; Analytical methods; Carbohydrates; Kinetics; UV/Vis spectroscopy.

Aldoses exist predominantly in the cyclic hemiacetal form, which is in equilibrium with the open-chain aldehyde form. The small aldehyde content hampers reactivity when chem. addresses the carbonyl moiety. This low concentration of the available aldehyde is generally difficult to ascertain. Herein, we demonstrate a new kinetic determination of the (minute) open-chain content (OCC) of aldoses. This kinetic approach exploits the aldehyde-selectivity of 2-aminobenzamidoxime (ABAO), which furnishes a strongly UV-active adduct. Simple formation curves can be measured in a photometer or plate reader for high-throughput screening. Under pseudo-first order kinetics, these curves correlate with a prediction model yielding the relative OCC. The OCCs of all parent aldoses (pentoses and hexoses) were determined referencing against the two tetroses with exceptionally high OCCs and were in very good agreement with literature data. Addnl., the assay was extended towards higher-carbon sugars with unknown OCC and also applied to rationalize a lack of reactivity observed in a recent synthetic investigation.

European Journal of Organic Chemistry published new progress about Aldoses Role: PRP (Properties), RCT (Reactant), RACT (Reactant or Reagent). 1885-29-6 belongs to class nitriles-buliding-blocks, name is 2-Aminobenzonitrile(Flakes or Chunks), and the molecular formula is C7H6N2, Safety of 2-Aminobenzonitrile(Flakes or Chunks).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Rousseaux, Sophie published the artcileIntramolecular Palladium-Catalyzed Alkane C-H Arylation from Aryl Chlorides, Safety of 2-(2-Chloro-4-methoxyphenyl)acetonitrile, the main research area is cyclobutarene indane indoline dihydrobenzofuran indanone preparation; alkane arylchloride intramol arylation palladium catalyst; DFT calculation computational study; arylation mechanism.

The first examples of efficient and general palladium-catalyzed intramol. C(sp3)-H arylation of (hetero)aryl chlorides, giving rise to a variety of valuable cyclobutarenes, indanes, indolines, dihydrobenzofurans, and indanones, are described. The use of aryl and heteroaryl chlorides significantly improves the scope of C(sp3)-H arylation by facilitating the preparation of reaction substrates. Careful optimization studies have shown that the palladium ligand and the base/solvent combination are crucial to obtaining the desired class of product in high yields. Overall, three sets of reaction conditions employing PtBu3, PCyp3, or PCy3 as the palladium ligand and K2CO3/DMF or Cs2CO3/pivalic acid/mesitylene as the base/solvent combination allowed five different classes of products to be accessed using this methodol. In total, more than 40 examples of C-H arylation have been performed successfully. When several types of C(sp3)-H bond were present in the substrate, the arylation was found to occur regioselectively at primary C-H bonds vs secondary or tertiary positions. In addition, in the presence of several primary C-H bonds, selectivity trends correlate with the size of the palladacyclic intermediate, with five-membered rings being favored over six- and seven-membered rings. Regio- and diastereoselectivity issues were studied computationally in the prototypal case of indane formation. DFT(B3PW91) calculations demonstrated that C-H activation is the rate-determining step and that the creation of a C-H agostic interaction, increasing the acidity of a geminal C-H bond, is a critical factor for the regiochem. control.

Journal of the American Chemical Society published new progress about Aromatic hydrocarbons Role: SPN (Synthetic Preparation), PREP (Preparation). 170737-93-6 belongs to class nitriles-buliding-blocks, name is 2-(2-Chloro-4-methoxyphenyl)acetonitrile, and the molecular formula is C9H8ClNO, Safety of 2-(2-Chloro-4-methoxyphenyl)acetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

More, Vijaykumar published the artcileThe first organocatalytic asymmetric synthesis of 3-substituted isoindolinones, Name: 2-Formyl-4,5-dimethoxybenzonitrile, the main research area is quinine cinchonidine urea thiourea alkaloid catalyst isoindolinone preparation.

Herein the authors describe the first asym. organocatalytic synthesis of 3-substituted isoindolinone derivatives by a convenient aldol-cyclization-rearrangement tandem reaction of malonates with 2-cyanobenzaldehyde. Bifunctional thiourea-cinchona catalysts proved to be particularly effective, giving the title compounds in high yield and moderate-to-good enantiomeric excesses. Moreover an efficient process of reverse crystallization led to a further enrichment up to >99% ee. The synthesis of the target compounds was achieved using N-[3,5-bis(trifluoromethyl)phenyl]-N’-[(8α,9S)-6′-methoxycinchonan-9-yl]thiourea, N-[3,5-bis(trifluoromethyl)phenyl]-N’-[(8α,9S)-cinchonan-9-yl]thiourea, etc. as catalysts in comparison with N-[3,5-bis(trifluoromethyl)phenyl]-N’-[(1R,2R)-2-(dimethylamino)cyclohexyl]thiourea, N-[3,5-bis(trifluoromethyl)phenyl]-N’-[(1S,2S)-2-(dimethylamino)-1-phenylpropyl]thiourea, cupreidine, etc. The title compounds thus formed included (-)-2-(2,3-dihydro-3-oxo-1H-isoindol-1-yl)-1,3-propanedioic acid 1,3-di-Me ester (I).

RSC Advances published new progress about Active methylene compounds Role: RCT (Reactant), RACT (Reactant or Reagent). 1013112-48-5 belongs to class nitriles-buliding-blocks, name is 2-Formyl-4,5-dimethoxybenzonitrile, and the molecular formula is C10H9NO3, Name: 2-Formyl-4,5-dimethoxybenzonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Vorobyev, P. B. published the artcileRole of theory acids and bases in the forming concepts of the mechanism catalytic oxidation and oxidative ammonolysis, Application of Picolinonitrile, the main research area is methyl pyridine catalytic oxidation oxidative ammonolysis.

Exptl. data of oxidation and oxidative ammonolysis the isomeric methylpyridines in the presence of vanadium oxide catalysts, it was found that the reactivity of substrates increases in the following sequence: 3-methylpyridine < 2-methylpyridine < 4-methylpyridine. The obtained exptl. results of relative reactivity of initial compounds were interpreted by the theory of acids and bases. It was shown that among the isomeric methylpyridines, increase of basicity which influence to adsorpting ability in the same order as the basicity and the CH-acidity of substrates calculated using non-empirical quantumchem. methods. Khimicheskii Zhurnal Kazakhstana published new progress about Acids Role: FMU (Formation, Unclassified), FORM (Formation, Nonpreparative). 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Application of Picolinonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Martinkova, Ludmila published the artcileEnantioselectivity of the nitrile hydratase from Rhodococcus equi A4 towards substituted (R,S)-2-arylpropionitriles, Name: 2-(3-Benzoylphenyl)propanenitrile, the main research area is nitrile hydratase enantioselectivity aryl propionitrile Rhodococcus; nitrilase enantioselectivity arylpropionitrile Rhodococcus.

Rhodococcus equi A4 cells containing a nitrile hydratase and an amidase converted (R,S)-2-(4-methoxyphenyl)-propionitrile into the corresponding (S)-acid (e.e. 87%) and (R)-nitrile (e.e. > 95%) in 49% yield. The same reaction using (R,S)-2-(4-chlorophenyl)-propionitrile gave the (S)-acid (e.e. > 95%) and (R)-nitrile (e.e. 52%) in 20 and 34% yield, resp.

Biotechnology Letters published new progress about Nitriles Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 42872-30-0 belongs to class nitriles-buliding-blocks, name is 2-(3-Benzoylphenyl)propanenitrile, and the molecular formula is C16H13NO, Name: 2-(3-Benzoylphenyl)propanenitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Chen, Shangqing published the artcileEfficient transformation of CO2 into quinazoline-2,4(1H,3H)-diones at room temperature catalyzed by a ZnI2/NEt3 system, Application of 2-Aminobenzonitrile(Flakes or Chunks), the main research area is aminobenzonitrile carbon dioxide zinc triethylamine cyclocondensation catalyst room temperature; quinazolinedione preparation.

The readily available ZnI2/NEt3 system was used firstly to catalyze the transformation of CO2 and 2-aminobenzonitriles into quinazoline-2,4(1H,3H)-diones at room temperature and low CO2 pressure in high yields. Further experiments indicated that this ZnI2/NEt3 system has excellent effects on activating both amino and cyano groups.

New Journal of Chemistry published new progress about Aromatic nitriles Role: RCT (Reactant), RACT (Reactant or Reagent) (2-amino). 1885-29-6 belongs to class nitriles-buliding-blocks, name is 2-Aminobenzonitrile(Flakes or Chunks), and the molecular formula is C7H6N2, Application of 2-Aminobenzonitrile(Flakes or Chunks).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts