Category: nitriles-buliding-blocks

Tobisu, Mamoru published the artcileRhodium(I)-Catalyzed Borylation of Nitriles through the Cleavage of Carbon-Cyano Bonds, SDS of cas: 214360-44-8, the publication is Journal of the American Chemical Society (2012), 134(1), 115-118, database is CAplus and MEDLINE.

The reaction of aryl cyanides with diboron in the presence of a [RhCl(cod)]₂/Xantphos catalyst and 1 equivalent DABCO affords arylboronic esters via C-cyano bond cleavage. E.g., reaction of PhCN with 2 equivalent of bis(neopentanediolato)diboron in the presence of 5 mol% [RhCl(cod)]₂/10 mol% Xantphos and 1 equivalent of DABCO in toluene at 100° to give 73% yield of 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane. This unprecedented mode of reactivity for a borylrhodium species allows the regioselective introduction of a boryl group in a late stage of synthesis.

Journal of the American Chemical Society 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 C6H9N3O2, SDS of cas: 214360-44-8.

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

Colvin, Ernest W. published the artcileO-(Diphenylphosphinyl)hydroxylamine: a new reagent for electrophilic C-amination, SDS of cas: 5098-14-6, the publication is Tetrahedron Letters (1982), 23(37), 3835-6, database is CAplus.

Ph₂P(O)ONH₂ (I) efficiently aminated (EtO)₂P(O)CH^–CO₂CH₂Ph, (EtO₂C)₂CH^–, (NC)₂CH^–, PhMgBr, and Me(CH₂)₅MgBr in THF at -78° under Ar. E.g., treatment of (EtO)₂P(O)CH₂CO₂CH₂Ph with NaH at room temperature under Ar, then I at -78° gave 60% (EtO)₂P(O)CH(NH₂)CO₂CH₂Ph.

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 C10H11N3O3S, SDS of cas: 5098-14-6.

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

Kinuta, Hirotaka published the artcileNovel synthetic approach to arylboronates via rhodium-catalyzed carbon-cyano bond cleavage of nitriles, Category: nitriles-buliding-blocks, the publication is Synthesis (2012), 44(19), 2999-3002, database is CAplus.

A new rhodium-catalyzed method for preparing arylboronates from aryl cyanides through the cleavage of carbon-cyano bonds is described. This unprecedented transformation of nitriles allows the use of a cyano group as a boryl equivalent and the regioselective introduction of a boryl group at a late stage of the synthesis.

Synthesis 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, Category: nitriles-buliding-blocks.

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

Tobisu, Mamoru published the artcileRhodium-catalyzed silylation and intramolecular arylation of nitriles via the silicon-assisted cleavage of carbon-cyano bonds, Name: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the publication is Journal of the American Chemical Society (2008), 130(47), 15982-15989, database is CAplus and MEDLINE.

Aryl and heterocyclic nitriles undergo substitution of the cyano-group by a silyl moiety in rhodium-catalyzed silylation by disilanes, yielding the corresponding aryl- and heterocyclic silanes. Reaction of RC₆H₄CN with Me₃SiSiMe₃ catalyzed by [Rh(cod)Cl]₂ or [Rh(OMe)(cod)]₂ gave the corresponding silylarenes, RC₆H₄SiMe₃ (R = 4-CF₃, 4-F, 4-CO₂Et, 4-CO₂^tBu, 4-CONH^tBu, 4-CONMe^tBu, 4-OAc, 4-OMe, 4-NMe₂, 3-OMe, 3-CO₂Et, 2-Me, 2-CF₃, 4-boronato). 2- And 1-Naphthalenecarbonitriles gave 2- and 1-naphthyltrimethylsilanes, resp. 1-Tosyl-2-pyrrolecarbonitrile, 1-tosyl-3-indolecarbonitrile, 3-quinolinecarbonitrile and ferrocenecarbonitrile were converted into the corresponding silanes with 57-81% yields. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from η²-iminoacyl complex. A new intramol. biaryl coupling reaction of 2-NCC₆H₄OC₆H₄X-2 (X = Br, Cl), giving dibenzofuran, in which aryl cyanides and aryl chlorides are cross-coupled, is developed.

Journal of the American Chemical Society 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 C3H5BN2O2, Name: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile.

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

Tobisu, Mamoru published the artcileRh(I)-Catalyzed Silylation of Aryl and Alkenyl Cyanides Involving the Cleavage of C-C and Si-Si Bonds, HPLC of Formula: 214360-44-8, the publication is Journal of the American Chemical Society (2006), 128(25), 8152-8153, database is CAplus and MEDLINE.

The Rh(I)-catalyzed silylation of nitriles with disilanes is described. The cleavage of inert carbon-cyano and silicon-silicon bonds occurs in this catalysis. Thus, [RhCl(COD)]₂-catalyzed silylation of 2-cyanonaphthalene with Me₃SiSiMe₃ in ethylcyclohexane at 130° for 15h gave 87% 2-trimethylsilylnaphthalene.

Journal of the American Chemical Society 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 C22H18Cl2N2, HPLC of Formula: 214360-44-8.

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

Sekikawa, Tohru published the artcileCatalytic Activity of epi-Quinine-Derived 3,5-Bis(trifluoromethyl)benzamide in Asymmetric Nitro-Michael Reaction of Furanones, SDS of cas: 5153-73-1, the publication is Organic Letters (2015), 17(12), 3026-3029, database is CAplus and MEDLINE.

High catalytic activity of novel epi-quinine-derived 3,5-bis(CF₃)benzamide in the asym. nitro-Michael reaction is described. With 0.1-5 mol % loadings of this catalyst, the addition of 5-substituted 2(3-H)-furanones to a wide range of nitroalkenes involving challenging substrates, β-alkylnitroalkenes, smoothly proceeded, giving the Michael adducts e. g., I, in high yields (>90%) with excellent diastereo- and enantioselectivity (>98:2 dr, syn major; 88-98% ee). DFT calculation was carried out to account for the high catalytic activity.

Organic Letters 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 C30H32ClN7O2, SDS of cas: 5153-73-1.

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

Bollier, Melanie published the artcileOne- or Two-Step Synthesis of C-8 and N-9 Substituted Purines, HPLC of Formula: 5098-14-6, the publication is Journal of Organic Chemistry (2018), 83(1), 422-430, database is CAplus and MEDLINE.

A novel and original strategy to obtain rapidly a large diversity of C-8 and N-9 substituted purines was developed. The present procedure describes annulation reactions in one or two steps starting from 5-aminoimidazole-4-carbonitriles 1–8 in moderate to good yields. 8,9-Disubstituted-6,9-dihydro-1H-purin-6-ones 9–14, 6-amino-8,9-disubstituted-3,9-dihydro-2H-purin-2-ones 15–20, 8,9-disubstituted-3,9-dihydro-2H-purin-2,6-diamines 21–24 and 6-imino-1-phenyl-8,9-disubstituted-6,9-dihydro-1H-purin-2-(3H)-ones 25–26 were synthesized in one step using formic acid, urea, guanidine carbonate, and Ph isocyanate, resp., whereas 8,9-disubstituted-9H-purin-6-amines 27–31 and 6-imino-8,9-disubstituted-6,9-dihydro-1H-purin-1-amines 32–33 were obtained in two steps using formamide and hydrazine, resp.

Journal of Organic 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, HPLC of Formula: 5098-14-6.

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

Noe, C. R. published the artcileAmino alcohols. II: Preparation of enantiomerically pure pharmacologically active β-amino alcohols, Computed Properties of 13312-84-0, the publication is Monatshefte fuer Chemie (1995), 126(4), 481-94, database is CAplus.

A synthesis of β-amino alcs. is described starting from racemic or enantiomerically pure α-hydroxynitriles which were O-protected using enantiomerically pure acetal type protective groups. Reduction with lithium aluminum hydride yielded O-protected β-amino alcs. Whenever diastereomeric O-protected cyanohydrins could not be separated, the mixture was reduced and the resulting O-protected amino alcs. were separated Removal of the protective group using hydrogen chloride and methanol yielded enantiomerically pure β-amino alcs. or their corresponding hydrochlorides. For example, the chiral synthesis of (R)-1-amino-3-(1-naphthalenyloxy)-2-propanol and (S)-1-amino-3-(1-naphthalenyloxy)-2-propanol was accomplished via resolution of (±)-2-hydroxy-3-(1-naphthalenyloxy)propanenitrile.

Monatshefte fuer Chemie 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, Computed Properties of 13312-84-0.

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

Noe, Christian R. published the artcileChiral lactols. XIII. On the determination of the absolute configuration of aromatic cyanohydrins and structurally related compounds, Quality Control of 13312-84-0, the publication is Liebigs Annalen (1995), 1353-60, database is CAplus.

Synthesis and conformational anal. of diastereomeric acetals, e.g. I, of aromatic cyanohydrins and structurally related compounds are described. Based on ¹H-NMR spectroscopic and x-ray data it is shown that the absolute configuration of such compounds can be assigned according to a method, which has been presented previously for secondary arylalkyl alcs.

Liebigs Annalen 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, Quality Control of 13312-84-0.

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

Kuroda, Chiaki published the artcileReaction of Aminomalononitrile and Benzylic Compounds as a Plausible Route to Phenylalanine, COA of Formula: C10H11N3O3S, the publication is Natural Product Communications (2020), 15(1), 1934578X20901417, database is CAplus.

As a possible route to phenylalanine, reaction of aminomalononitrile with benzylic compounds was studied. 2-Benzyl-2-aminomalononitrile was obtained in a good yield when aminomalononitrile p-toluenesulfonate was treated with benzyl bromide in THF using triethylamine as a base. The reaction proceeded in the presence of water. 2-Benzyl-2-aminomalononitrile was hydrolyzed to afford phenylalanine. The aminomalononitrile route can explain the presence of not only 1 methylene in aromatic amino acids, but also α-hydrogen in all 20 proteinogenic amino acids.

Natural Product Communications 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, COA of Formula: C10H11N3O3S.

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