Month: December 2022

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

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

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

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

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.

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.

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

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.

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 C12H14BNO2, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile.

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

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.

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, COA of Formula: C10H11N3O3S.

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

Freeman, Fillmore published the artcilePreparation of (E,E)-4-amino-1-aryl-3-cyano-4-methoxy-2-azabutadienes, Formula: C10H11N3O3S, the publication is Synthesis (1989), 698-9, database is CAplus.

Treatment of (NC)₂CHN⁺H₃ 4-MeC₆H₄SO₃^– with NaOAc and RCHO (R = Ph, 2-BrC₆H₄, 2-ClC₆H₄, 2-O₂NC₆H₄, 4-O₂NC₆H₄, 4-HOC₆H₄, 2-naphthyl) in MeOH gave 23-99% (E,E)-RCH:NC(CN):C(OMe)NH₂.

Synthesis 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, Formula: C10H11N3O3S.

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

Freeman, Fillmore published the artcileReaction of aminopropanedinitrile 4-methylbenzenesulfonate (aminomalononitrile p-toluenesulfonate (tosylate)) with isothiocyanates, Computed Properties of 5098-14-6, the publication is Journal of Organic Chemistry (1991), 56(15), 4645-8, database is CAplus.

Aminopropanedinitrile tosylate reacts with isothiocyanates RNCS (R = Bu, 4-MeOC₆H₄, Ph, 4-ClC₆H₄, 4-O₂NC₆H₄, 1-naphthyl) in 1-methyl-2-pyrrolidinone to give 2,5-diaminothiazole-4-carbonitriles I. I (R = 4-MeOC₆H₄, Ph) react with H₂NCH:NH.AcOH to give thiazolopyrimidines II (R¹ = H). I (R = Ph) also reacts with MeC(OEt)₃ to give II (R = Ph, R¹ = Me).

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, Computed Properties of 5098-14-6.

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

Freeman, Fillmore published the artcileReaction of aminopropanedinitrile 4-methylbenzenesulfonate [aminomalononitrile p-toluenesulfonate (tosylate)] with aromatic aldehydes, SDS of cas: 5098-14-6, the publication is Journal of Organic Chemistry (1991), 56(2), 657-63, database is CAplus.

(NC)₂CHNH₂·HO₃SC₆H₄Me-4 reacts with aromatic aldehydes in NaOAc-MeOH to give diastereoselectively (E,E)-RCH:NC(CN):C(NH₂)OMe (R = C₆H₄R¹-4, R¹ = OMe, OEt, OAc, H, Br, NO₂, CO₂Me; R = 3-pyridyl, 3-thienyl) and trans-3,6-diaryl-2,2,5,5-tetracyanopiperazines I (same R). The product distribution depends on the ratio of reactants and the structures of the substrates. Electron-releasing groups on the 4-position of the Ph ring favor piperazine formation. The formation of piperazines may involve synthetically useful N-protonated aryl- and cyano-stabilized azomethine ylide (prototropic 1,3-dipoles) intermediates which could have resulted from an imine-azomethine ylide tautomerism of prior formed 1-aryl-3,3-dicyano-2-aza-1-propenes. [4+2]-1,3-Dipolar cycloaddition reactions of the highly reactive azomethine ylides with MeO₂CCCCO₂Me give 3,4-dicarbomethoxy-2-cyano-5-aryl-3-pyrrolines, which undergo facile dehydrocyanation to 3,4-dicarbomethoxy-2-cyano-5-arylpyrroles. The possible intermediacy of ketenimines and of aryl- and cyano-stabilized 2-azaallyl anionic intermediates in equilibrium with azomethine ylides is also considered.

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, SDS of cas: 5098-14-6.

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