Month: December 2022

Wang, Hai-Jun published the artcilePd/C-Catalyzed Dehydrogenative [3+2] Cycloaddition for the Synthesis of Functionalized Tropanes, Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is European Journal of Organic Chemistry (2018), 2018(39), 5456-5459, database is CAplus.

A Pd/C-catalyzed cascade approach for the synthesis of attractive benzo-fused tropanes was developed. The reaction proceeds through a sequential Pd/C-catalyzed dehydrogenative formation of azomethine ylides from amines and 1,3-dipolar cycloaddition It gave structurally complex benzo-fused tropanes in good yields with excellent diastereoselectivities under mild reaction conditions. Preliminary results of asym. version of the reaction reveal that the copper catalyst and chiral monophosphoramidite ligand can furnish optically active products with moderate ee.

European Journal of Organic Chemistry published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C6H5BFNO4, Name: (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Rani, Dixita published the artcileAqueous synthesis of 2-aryl-3-nitro-2H-chromenes via L-prolinamide mediated tandem oxa-Michael Henry reactions, Category: nitriles-buliding-blocks, the publication is Journal of Molecular Structure (2022), 133341, database is CAplus.

An efficient and aqueous protocol was developed for the synthesis of 2-aryl-3-nitro-2H-chromene derivatives This protocol involves the L-prolinamide mediated tandem oxa-Michael Henry reaction between a variety of β-nitrostyrenes and salicylaldehyde. Among the screened solvents, the catalytic efficiency of prolinamides was found to be high in chloroform, but the best results were obtained in water to provide the 2-phenyl-3-nitro-2H-chromene in excellent yields. Substrate scope was also investigated using various substituted β-Nitrostyrenes. All reactions worked well to provide the corresponding products in very high yields. Theor. calculations were performed to find out the reaction pathways and nature of transition state at 3-21G* basis set and TS1 corresponding to the product (S)-3a, was found favorable by 1.13 kcal/mol over TS2 corresponding to the product (R)-3a.

Journal of Molecular Structure published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Li, Si-Yuan published the artcilePractical copper-catalyzed chloronitration of alkenes with TMSCl and guanidine nitrate, Quality Control of 5153-73-1, the publication is Organic Chemistry Frontiers (2020), 7(17), 2449-2455, database is CAplus.

A novel and practical chloronitration of alkenes in the presence of easily available TMSCl and guanidine nitrate was developed by using cheap copper sulfate pentahydrate as the catalyst. A variety of vic-chloronitro compounds were directly synthesized in good to excellent yields on up to 100 mmol scale under mild reaction conditions, and the resulting products could be smoothly transformed into the corresponding nitroalkenes and diverse nitro compounds bearing a vicinal nucleophilic “C”, “N” or “S” unit.

Organic Chemistry Frontiers published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Quality Control of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

McEwen, William E. published the artcileSynthetic uses of open-chain analogs of Reissert compounds, Related Products of nitriles-buliding-blocks, the publication is Journal of Organic Chemistry (1980), 45(7), 1301-8, database is CAplus.

Open-chain analogs, RN(COR²)CHR¹CN (I, R = Ph, PhCH₂, p-ClC₆H₄, p-MeOC₆H₄, Me(CH₂)₅, cyclohexyl; R¹ = Ph, H, o-, m-, p-ClC₆H₄, 3,4-(MeO)₂C₆H₃, o-, m-MeOC₆H₄, Bu; R² = Ph, Me), of Reissert compounds are obtained by reaction of R¹CH(OH)CN with RNH₂, the resulting aminonitriles, RNHCHR¹CN, then being acylated. Hydrofluoroborate salts, II, of I, are prepared by reaction with fluoroboric acid in HOAc. The salts, II, undergo 1,3-dipolar addition reactions with reactive alkynes to give substituted pyrroles and with Et acrylate to give a different type of substituted pyrrole, the initial step in this instance being a Diels-Alder reaction. Thus, addition of MeO₂CCCCO₂Me to II (R¹ = R² = Ph) gave III (R = Ph, m-ClC₆H₄, p-MeOC₆H₄, PhCH₂); and addition of H₂C:CHCO₂Et to II (R = R¹ = R² = Ph) gave IV. I also undergo base-catalyzed reactions, such as alkylation with R⁵Br to provide R²CONRCR¹R⁵CN (R⁵ = PhCH₂, Bu, α-naphthylmethyl, R-R² = as above), which, in turn, undergo cleavage reactions in ethanolic alkali to give ketones R¹R⁵CO. A conjugate addition reaction of the anion BzNPhC^–PhCN (V) to Me acrylate to give, after subsequent steps, VI was demonstrated. α-Anilino ketones, PhNHCHRCOR¹, result when the anion V is treated with aldehydes, the initial reaction mixtures being subjected to subsequent alk. hydrolysis. Finally, N-benzyl Reissert analogs give desoxybenzoins plus benzonitriles on treatment with NaH in THF.

Journal of Organic Chemistry published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Fairley, Gary published the artcileOne-pot synthesis of novel 1,2,6,7-tetrahydro-3H-pyrazolo[4,3-c]pyridine-3,4(5H)-diones, SDS of cas: 49540-34-3, the publication is Tetrahedron Letters (2018), 59(39), 3574-3578, database is CAplus.

A facile synthesis of novel 1,2,6,7-tetrahydro-3H-pyrazolo[4,3-c]pyridine-3,4(5H)-diones was achieved. The operationally simple procedure, using readily available intermediates, allows for rapid derivatization of the pharmacophore with alkyl, aryl and heteroaryl substituents.

Tetrahedron Letters published new progress about 49540-34-3. 49540-34-3 belongs to nitriles-buliding-blocks, auxiliary class Aliphatic Chain, name is Ethylhydrazine dihydrochloride, and the molecular formula is C2H10Cl2N2, SDS of cas: 49540-34-3.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kang, Taeho published the artcileAlkene Difunctionalization Directed by Free Amines: Diamine Synthesis via Nickel-Catalyzed 1,2-Carboamination, SDS of cas: 214360-44-8, the publication is ACS Catalysis (2022), 12(7), 3890-3896, database is CAplus.

A versatile method to access differentially substituted 1,3- and 1,4-diamines RNH(CH₂)₂CH(R¹)CH₂R² (R = H, Me, Bn, pyrimidin-2-yl, etc.; R¹ = piperidin-1-yl, 1,4-dioxa-8-azaspiro[4.5]decan-8-yl, diethylaminyl; R² = Ph, naphthalen-1-yl, 1-benzofuran-5-yl, etc.) via a nickel-catalyzed three-component 1,2-carboamination of alkenyl amines RNH(CH₂)₂CH=CH₂ with aryl/alkenylboronic ester nucleophiles R³COOR¹ (R³ = t-Bu, Ph, morpholin-4-yl, etc.) and N-O electrophiles R²B(nep) was reported. The reaction proceeds efficiently with free primary and secondary amines without needing a directing auxiliary or protecting group, and is enabled by fine-tuning the leaving group on the N-O reagent. The transformation is highly regioselective and compatible with a wide range of coupling partners and alkenyl amine substrates, all performed at room temperature A series of kinetic studies support a mechanism in which alkene coordination to the nickel catalyst is turnover-limiting.

ACS Catalysis published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, SDS of cas: 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Nikseresht, Ahmad published the artcile[Cu₃(BTC)₂]: A metal-organic framework as an environment-friendly and economically catalyst for the synthesis of tacrine analogues by Friedlaender reaction under conventional and ultrasound irradiation, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Polyhedron (2018), 112-117, database is CAplus.

Using a green and simple route with ultrasound illumination, atm. pressure and room temperature, for synthesizing tacrine analogs in the presence of [Cu₃(BTC)₂] as an environment-friendly and economically catalyst was considered. [Cu₃(BTC)₂] is one of the heterogeneous catalysts on hand capable of being employed, in the Friedlaender reaction, whenever 5-amino-4-cyano-2-phenyl-1,3-oxazole and appropriately substituted carbonyl derivatives under conventional and ultrasonic irradiation The results of this study indicate that the active sites in the [Cu₃(BTC)₂] for synthesis of cyclohepta[b]oxazolo[4,5-e]pyridine are mainly copper atoms and the role of Bronsted acid organic ligand in the MOF is negligible. These procedures were properly arranged to provide the utmost yields in a short while. The crystal stability in the process of catalysis was studied by various techniques such as XRD, BET and ICP that demonstrate excellent stability in reaction conditions.

Polyhedron published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wang, Hualei published the artcileProtein engineering of a nitrilase from Burkholderia cenocepacia J2315 for efficient and enantioselective production of (R)-o-chloromandelic acid, Related Products of nitriles-buliding-blocks, the publication is Applied and Environmental Microbiology (2015), 81(24), 8469-8477, database is CAplus and MEDLINE.

The nitrilase-mediated pathway has significant advantages in the production of optically pure aromatic α-hydroxy carboxylic acids. However, low enantioselectivity and activity are observed on hydrolyzing o-chloromandelonitrile to produce optically pure (R)-o-chloromandelic acid. A protein engineering approach was successfully used to enhance the performance of nitrilase obtained from Burkholderia cenocepacia strain J2315 (BCJ2315) in hydrolyzing o-chloromandelonitrile. Four hot spots (T49, I113, Y199, and T310) responsible for the enantioselectivity and activity of BCJ2315 were identified by random mutagenesis. An effective double mutant (I113M/Y199G [encoding the replacement of I with M at position 113 and Y with G at position 199]), which demonstrated remarkably enhanced enantioselectivity (99.1% enantiomeric excess [ee] compared to 89.2% ee for the wild type) and relative activity (360% of the wild type), was created by two rounds of site saturation mutagenesis, first at each of the four hot spots and subsequently at position 199 for combination with the selected beneficial mutation I113M. Notably, this mutant also demonstrated dramatically enhanced enantioselectivity and activity toward other mandelonitrile derivatives and, thus, broadened the substrate scope of this nitrilase. Using an Et acetate-water (1:9) biphasic system, o-chloromandelonitrile (500 mM) was completely hydrolyzed in 3 h by this mutant with a small amount of biocatalyst (10 g/L wet cells), resulting in a high concentration of (R)-o-chloromandelic acid with 98.7% ee, to the authors’ knowledge the highest ever reported. This result highlights a promising method for industrial production of optically pure (R)-o-chloromandelic acid. Insight into the source of enantioselectivity and activity was gained by homol. modeling and mol. docking experiments

Applied and Environmental Microbiology published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C18H10, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Sun, Huihui published the artcileCloning, purification and evaluation of the enzymatic properties of a novel arylacetonitrilase from Luminiphilus syltensis NOR5-1B: a potential biocatalyst for the synthesis of mandelic acid and its derivatives, Category: nitriles-buliding-blocks, the publication is Biotechnology Letters (2015), 37(8), 1655-1661, database is CAplus and MEDLINE.

Objective: To examine nitrilase-mediated hydrolysis of nitriles to produce optically pure α-hydroxycarboxylic acids. Results: A novel nitrilase, GPnor51, from Luminiphilus syltensis NOR5-1B was discovered by genomic data mining. It could hydrolyze racemic o-chloromandelonitrile to (R)-o-chloromandelic acid with high enantioselectivity (ee 98.2 %). GPnor51 was overexpressed in Escherichia coli BL21 (DE3), purified, and its catalytic properties studied. GPnor51 had a broad substrate acceptance toward various nitriles with structure diversity. It was an arylacetonitrilase that uses arylacetonitriles as optimal substrates. The V_max and K_m of GPnor51 towards o-chloromandelonitrile were 1.9 μmol min^-1 mg^-1 protein and 0.38 mM, resp. GPnor51 also demonstrated high enantioselectivity toward mandelonitrile and other substituted mandelonitrile. Conclusion: This enzyme has a great potential for com. production of optically pure (R)-mandelic acid and its derivatives

Biotechnology Letters published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C10H13NO2, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts