Author: Jessica.F

Zhang, Wenjun published the artcileSynthesis of aryl acetamides by aminocarbonylation of benzylic chlorides using carbamoylsilane as an amide source, SDS of cas: 612-13-5, the publication is Synthetic Communications (2017), 47(7), 704-709, database is CAplus.

Using N-methyl-N-(1-phenyl)ethylcarbamoyl(trimethyl)silane as an amide source, the direct transformation of benzylic chlorides into the corresponding aryl acetamides through palladium-catalyzed aminocarbonylation is described. The electronic property and the relative position of substituents on the aromatic ring impact the coupling efficiency.

Synthetic Communications published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C5H5BrN2, SDS of cas: 612-13-5.

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

Mills, L. Reginald published the artcileCobalt-Catalyzed C(sp²)-C(sp³) Suzuki-Miyaura Cross-Coupling Enabled by Well-Defined Precatalysts with L,X-Type Ligands, Quality Control of 214360-44-8, the publication is ACS Catalysis (2022), 12(3), 1905-1918, database is CAplus and MEDLINE.

Cobalt(II) halides in combination with phenoxyimine (FI) ligands generated efficient precatalysts in situ for the C(sp²)-C(sp³) Suzuki-Miyaura cross-coupling between alkyl bromides and neopentylglycol (hetero)arylboronic esters. The protocol enabled efficient C-C bond formation with a host of nucleophiles and electrophiles (36 examples, 34-95%) with precatalyst loadings of 5 mol %. Studies with alkyl halide electrophiles that function as radical clocks support the intermediacy of alkyl radicals during the course of the catalytic reaction. The improved performance of the FI-cobalt catalyst was correlated with decreased lifetimes of cage-escaped radicals as compared to those of diamine-type ligands. Studies of the phenoxy(imine)-cobalt coordination chem. validate the L,X interaction leading to the discovery of an optimal, well-defined, air-stable mono-FI-cobalt(II) precatalyst structure.

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, Quality Control of 214360-44-8.

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

Deng, Lijuan published the artcileLigustrazine derivatives. Part 4: Design, synthesis, and biological evaluation of novel ligustrazine-based stilbene derivatives as potential cardiovascular agents, Synthetic Route of 612-13-5, the publication is Chemical Biology & Drug Design (2012), 79(5), 731-739, database is CAplus and MEDLINE.

A series of novel stilbene derivatives containing ligustrazinyl moiety was designed, synthesized, and assayed for their protective effects on damaged endothelial cells. The results showed that most ligustrazinyl stilbene derivatives exhibited high protective effects on the human umbilical vascular endothelial cells (HUVECs) damaged by hydrogen peroxide in comparison with Ligustrazine. Structure-activity relationships were briefly discussed.

Chemical Biology & Drug Design published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Synthetic Route of 612-13-5.

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

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