Author: Jessica.F

Juhl, Martin published the artcileCO₂-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions, Category: nitriles-buliding-blocks, the publication is Chemistry – A European Journal (2021), 27(1), 228-232, database is CAplus and MEDLINE.

Use of carbon dioxide/carbon disulfide to accelerate cyanohydrin RR¹COHCN [R = cyclohexyl, Ph, 2-furyl, etc.; R¹ = H, CO₂H] and R²CHOC(S)SMeCN [R² = 4-FC₆H₄, (CH₂)₂Ph] syntheses starting from alkyl- and aryl aldehydes under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN were reported. Under inert atm., the reaction was essentially not operative due to the unfavored equilibrium The utility of CO₂-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani-Fischer synthesis under neutral conditions. This protocol offered an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atm. pressure of CO².

Chemistry – A European Journal 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, Category: nitriles-buliding-blocks.

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

Taylor, Edward C. published the artcilePteridines. XXIX. Unequivocal route to 2,4-diamino-6-substituted pteridines, Application In Synthesis of 5098-14-6, the publication is Journal of the American Chemical Society (1973), 95(19), 6413-18, database is CAplus.

2,4-Diamino-6-substituted pteridines (I) are prepared Reaction of an α-keto-aldoxime with aminomalononitrile gives 2-amino-3-cyano-5-substituted pyrazine 1-oxides which yield 2,4-diamino-6-substituted pteridine 8-oxides upon cyclization with guanidine. 2,4-Diaminopteridines are then obtained by deoxygenation of the corresponding 8-oxides, or alternately by prior deoxygenation of these pyrazine 1-oxides, followed by cyclization with guanidine. The conversion of 2-amino-3-cyano-5-methylpyrazine 1-oxide to the corresponding 1,4-dioxide, and a number of chem. transformations of this latter intermediate, are also described.

Journal of the American Chemical Society 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 C3H8N2S, Application In Synthesis of 5098-14-6.

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

Baraldi, Pier Giovanni published the artcileAntimicrobial and antitumor activity of N-heteroimmine-1,2,3-dithiazoles and their transformation in triazolo-, imidazo-, and pyrazolopyrimidines, Related Products of nitriles-buliding-blocks, the publication is Bioorganic & Medicinal Chemistry (2001), 10(2), 449-456, database is CAplus and MEDLINE.

The reaction of Appel’s salt with o-aminonitrile heterocyclics gave the corresponding 4-chloro-5-heteroimmine-1,2,3-dithiazoles which were evaluated for their antibacterial, antifungal and antitumor activity. Although all these N-heteroimines were devoid of significant antibacterial activity, they showed significant antifungal activity. Moreover, the same derivatives represent highly versatile intermediates in heterocyclic synthesis, in fact the pyrazoleiminodithiazoles can be converted in one step into 2-cyano derivatives of the corresponding 4-methoxy-pyrazolo[3,4-d]pyrimidines by sodium methoxide in refluxing methanol. This provides a general and attractive route to 4-methoxy-6-cyanopyrazolo[3,4-d]pyrimidines from 1-substituted 5-amino pyrazoles in two simple steps. Finally, the isosteric replacement of the pyrazole ring atoms to give the imidazole[3,4-d]pyrimidine and triazole [4,5-d]pyrimidine ring systems was examined

Bioorganic & Medicinal Chemistry 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, Related Products of nitriles-buliding-blocks.

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

Spencer, John published the artcileMicrowave-mediated synthesis and manipulation of a 2-substituted-5-aminooxazole-4-carbonitrile library, Application of 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Tetrahedron Letters (2012), 53(13), 1656-1659, database is CAplus.

A 2-substituted 5-aminooxazole-4-carbonitrile library has been synthesized and modified via microwave-mediated and flow chemistries. One synthesized compound, 5-(1H-pyrrol-1-yl)-4-(1H-tetrazol-5-yl)-2-(thien-2-yl)oxazole, contains three distinct heterocycles attached to the central oxazole core, highlighting the structural diversity of this approach. Three oxazoles had micromolar k_i values against cannabinoid (CB1/CB2) receptors.

Tetrahedron Letters 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 C12H13BrN2O2, Application of 2-Aminomalononitrile 4-methylbenzenesulfonate.

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

Back, Jisu published the artcileTriazenyl Radicals Stabilized by N-Heterocyclic Carbenes, COA of Formula: C10H12F6N4O6PdS2, the publication is Journal of the American Chemical Society (2017), 139(43), 15300-15303, database is CAplus and MEDLINE.

Notwithstanding the notable progress in the synthesis of N-heterocyclic carbene-stabilized radicals, aminyl radicals, supported by NHCs or otherwise, were scarcely studied due to synthetic challenges. Triazenyl radical is a particular form of aminyl radical that contains three adjacent N atoms, and offers intriguing possibilities for unique reactivity and phys. properties stemming from expected delocalization of the spin d. over the NNN moiety and its conjugated substituents. Here, the authors report the synthesis and full characterization of the 1st NHC-stabilized triazenyl radicals, obtained by 1-electron reduction of the corresponding triazenyl cations with K metal. These radicals reversibly oxidize back to the cations upon treatment with transition metal sources or electrophiles, and abstract H atom from xanthene to form a new N-H bond at the center N atom. Potential application of the redox couple between triazenyl cation and triazenyl radical was demonstrated as cathode active materials in Li ion batteries.

Journal of the American Chemical Society published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, COA of Formula: C10H12F6N4O6PdS2.

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

Plaza, Manuel published the artcileHeterocyclization and Spirocyclization Processes Based on Domino Reactions of N-Tosylhydrazones and Boronic Acids Involving Intramolecular Allylborylations of Nitriles, Quality Control of 238088-16-9, the publication is Chemistry – A European Journal (2018), 24(55), 14836-14843, database is CAplus and MEDLINE.

Polycyclic mols. featuring all-carbon quaternary bridgehead centers were synthesized through domino cyclizations between N-tosylhydrazones and boronic acids. Variations of the general cascade have been applied for the preparation of 3-quinuclidinones and related alkaloid-like scaffolds through transannular heterocyclizations. Moreover, the employment of 3-cyanopropyl and 4-cyanobutylboronic acids and α,β-unsaturated N-tosylhydrazones led to spirocycles through unprecedented formal [n+1] cyclizations, including the stereoselective spirocyclization of the Hajos-Parrish ketone. The common feature of all the new reactions described is the creation of an all-carbon quaternary center by formation of two Csp³-C bonds on the hydrazonic carbon atom. DFT-based calculations suggested the occurrence of cascade processes, which involve a diazo compound carboborylation followed by a 1,3-borotropic rearrangement on an intermediate allylboronic acid and a novel bora-aza-ene cyclization.

Chemistry – A European Journal published new progress about 238088-16-9. 238088-16-9 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Aliphatic cyclic hydrocarbon,Boronic Acids,Boronate Esters, name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, and the molecular formula is C10H18BNO2, Quality Control of 238088-16-9.

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

Parekh, Hansa published the artcilePreparation and resolution of (+-)-p-(α-cyanoarylamino)benzoic acid, Synthetic Route of 13312-84-0, the publication is Indian Journal of Chemistry (1973), 11(5), 501-3, database is CAplus.

α-Amino nitriles (±)-RCH(CN)NHC6H4COOH-p [(±)I:R = Ph, o-ClC6H4, p-MeOC6H4] were prepared by condensing an aldehyde cyanhydrin with p-aminobenzoic acid. The resolution of (±)(I) into optical isomers was accomplished through fractional crystallization of the brucine salts to give the resp. (-)-nitriles. With (±)-I (R = p-MeOC6H4), the (+)-nitrile was also obtained. The introduction of Cl in the Ph nucleus at the ortho-position enhanced the optical activity, while the MeO group at the paraposition decreased the optical activity.

Indian Journal of 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, Synthetic Route of 13312-84-0.

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

Zhang, Zhi-Jun published the artcileSignificant enhancement of (R)-mandelic acid production by relieving substrate inhibition of recombinant nitrilase in toluene-water biphasic system, Computed Properties of 13312-84-0, the publication is Journal of Biotechnology (2011), 152(1-2), 24-29, database is CAplus and MEDLINE.

The enantioselective hydrolysis of mandelonitrile with whole cells of a recombinant Escherichia coli expressing nitrilase activity was severely inhibited by the substrate at high concentrations (>300 mM), which resulted in a low yield of the target product (R)-(-)-mandelic acid. To relieve the substrate inhibition and to enhance the (R)-(-)-mandelic acid productivity, eight water-organic solvent biphasic systems were attempted in this work. Toluene was found to be the most suitable solvent as the organic phase among the solvents tested. Various parameters were systematically examined and optimized in shake flasks. The phase volume ratio, buffer pH and reaction temperature were shown to be sensitive parameters affecting both the yield and the enantiopurity of product in the biphasic system. Under the optimized conditions, significant enhancement of substrate tolerance from 200 mM to 500 mM and average productivity from 179.6 g L^-1 d^-1 to 352.6 g L^-1 d^-1 were achieved. Subsequently, the biocatalytic hydrolysis of mandelonitrile was successfully carried out in a stirred reactor (2-L scale) by repeated use of the calcium alginate entrapped cells for 5 batches, affording 110.7 g (R)-(-)-mandelic acid in 98.0% ee (enantiomeric excess) and a specific production of 13.8 g (mandelic acid) g^-1 (cell), resp.

Journal of Biotechnology 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 C14H26O2, Computed Properties of 13312-84-0.

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

Moon, Lomary S. published the artcileChiral Solvating Agents for Cyanohydrins and Carboxylic Acids, SDS of cas: 13312-84-0, the publication is Journal of Organic Chemistry (2010), 75(16), 5487-5498, database is CAplus and MEDLINE.

A structure as simple as an ion pair of (R)- or (S)-mandelate and dimethylamminopyridinium ions possesses structural features that are sufficient for NMR enantiodiscrimination of cyanohydrins. Also, ¹H NMR data of cyanohydrins of known configuration obtained in the presence of the mandelate-dimethylaminopyridinium ion pair point to the existence of a correlation between chem. shifts and absolute configuration of cyanohydrins. Mandelate-DMAPH⁺ ion pair and mandelonitrile form a 1:1 complex with an association constant of 338 M^-1 (ΔG⁰, -3.4 kcal/mol) for the (R)-mandelonitrile/(R)-mandelate-DMAPH⁺ and 139 M^-1 (ΔG⁰, -2.9 kcal/mol) for the (R)-mandelonitrile/(S)-mandelate-DMAPH⁺ complex. To understand the origin of enantiodiscrimination, the geometry optimization and energy minimization of the models of ternary complexes of (S)-mandelonitrile/(R)-mandelate/DMAPH⁺ and (S)-mandelonitrile/(S)-mandelate/DMAPH⁺ complexes was performed using DFT methodol. (B3LYP) with the 6-31+G(d) basis set in Gaussian 3.0. Further, anal. of optimized mol. model obtained from theor. studies suggested that (i) DMAP may be replaced with other amines, (ii) the hydroxyl group of mandelic acid is not necessary for stabilization of ternary complex and may be replaced with other groups such as Me, (iii) the ion pair should form a stable ternary complex with any hydrogen-bond donor, provided its OH bond is sufficiently polarized, and (iv) α-H of racemic mandelic acid should also get resolved with optically pure mandelonitrile. These inferences were exptl. verified, which not only validated the proposed model but also led to development of a new chiral solvating agent for determination of ee of carboxylic acids and absolute configuration of aryl but not alkyl carboxylic acids.

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, SDS of cas: 13312-84-0.

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

Ferris, James P. published the artcileAminomalononitrile and 4-amino-5-cyanoimidazole in hydrogen cyanide polymerization and adenine synthesis, Product Details of C10H11N3O3S, the publication is Journal of the American Chemical Society (1965), 87(21), 4976-7, database is CAplus and MEDLINE.

Aminomalononitrile (I) was prepared by the treatment of oximinomalononitrile with Al-Hg; p-toluenesulfonate derivative m. 180-1°. Treatment of I with acid anhydride gave the corresponding oxazoles (II). I is converted to III by reaction with formamidine acetate (IV). Further treatment of III with IV gave adenine. KCN and I react at pH 9-10 to give a brown polymer and diaminomaleonitrile (V). V is the most prominent low-mol.-weight product formed during the polymerization of HCN. The results indicate that I is a key intermediate in HCN polymerizations and possibly prebiol. organic synthesis.

Journal of the American Chemical Society 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, Product Details of C10H11N3O3S.

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