Jessica.F

Bollier, Melanie’s team published research in Journal of Organic Chemistry in 83 | CAS: 5098-14-6

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.

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.

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

Sekikawa, Tohru’s team published research in Organic Letters in 17 | CAS: 5153-73-1

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.

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.

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

Tobisu, Mamoru’s team published research in Journal of the American Chemical Society in 128 | CAS: 214360-44-8

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.

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.

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

Tobisu, Mamoru’s team published research in Journal of the American Chemical Society in 130 | CAS: 214360-44-8

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.

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

Kinuta, Hirotaka’s team published research in Synthesis in 44 | CAS: 214360-44-8

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.

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.

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

Colvin, Ernest W.’s team published research in Tetrahedron Letters in 23 | CAS: 5098-14-6

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.

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.

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

Tobisu, Mamoru’s team published research in Journal of the American Chemical Society in 134 | CAS: 214360-44-8

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.

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

Lim, Ji Woong’s team published research in European Journal of Medicinal Chemistry in 157 | CAS: 612-13-5

European Journal of Medicinal Chemistry 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, COA of Formula: C8H6ClN.

Lim, Ji Woong published the artcileIdentification of crizotinib derivatives as potent SHIP2 inhibitors for the treatment of Alzheimer’s disease, COA of Formula: C8H6ClN, the publication is European Journal of Medicinal Chemistry (2018), 405-422, database is CAplus and MEDLINE.

SH2 domain-containing inositol 5′-phosphatase 2 (SHIP2) is a lipid phosphatase that produces phosphatidylinositol 3,4-bisphosphate (PI(3,4)P₂) from phosphatidylinositol 3,4,5-triphosphate (PI(3,4,5)P₃), and is involved in many diseases such as neurodegenerative diseases. A recent report demonstrating that SHIP2 inhibition decreased tau hyperphosphorylation induced by amyloid β and rescued memory impairment in a transgenic Alzheimer’s disease mouse model indicates SHIP2 can be a promising therapeutic target for Alzheimer’s disease. In the present study, the authors have developed novel, potent SHIP2 inhibitors by extensive structural elaboration of crizotinib discovered from a high-throughput screening. The authors’ representative compound 43 ((R)-5-(5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)pyrimidin-2-amine) potently inhibited SHIP2 activity as well as GSK3β activation in HT22 neuronal cells. It was also shown that 43 has favorable physicochem. properties, especially high brain penetration. Considering SHIP2 is one of key signal mediators for tau hyperphosphorylation, the authors’ potent SHIP2 inhibitor 43 may function as a promising lead compound for the treatment of Alzheimer’s disease.

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

Kang, Taeho’s team published research in Journal of the American Chemical Society in 143 | CAS: 214360-44-8

Kang, Taeho published the artcileNickel-Catalyzed 1,2-Carboamination of Alkenyl Alcohols, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the publication is Journal of the American Chemical Society (2021), 143(34), 13962-13970, database is CAplus and MEDLINE.

An alc.-directed, nickel-catalyzed three-component umpolung carboamination of unactivated alkenes with aryl/alkenylboronic esters and electrophilic aminating reagents was reported. This transformation was enabled by specifically tailored O-(2,6-dimethoxybenzoyl)hydroxylamine electrophiles that suppressed competitive processes, including undesired β-hydride elimination and transesterification between the alc. substrate and electrophile. The reaction delivered the desired 1,2-carboaminated products with generally high regio- and syn-diastereoselectivity and exhibited a broad scope of coupling partners and alkenes, including complex natural products. Various mechanistic experiments and anal. of the stereochem. outcome with a cyclic alkene substrate, as confirmed by X-ray crystallog. anal., support alc.-directed syn-insertion of an organonickel(I) species.

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

Freeman, Fillmore’s team published research in Tetrahedron Letters in 30 | CAS: 5098-14-6

Freeman, Fillmore published the artcilePreparation of 2-alkyl- and 2-aryl-5-amino-4-cyano-1,3-oxazoles, COA of Formula: C10H11N3O3S, the publication is Tetrahedron Letters (1989), 30(20), 2631-2, database is CAplus.

Aminopropanedinitrile p-toluenesulfonate reacts with acid chlorides to give 5-amino-4-cyano-1,3-oxazoles I (R = Me, Et, CHMe₂, Ph, 4-MeOC₆H₄, 4-O₂NC₆H₄, 2-furyl) in 51-95% yields.

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