Author: Jessica.F

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

Komeyama, Kimihiro published the artcileThe drastic effect of cobalt and chromium catalysts in the borylation of arylzinc reagents, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the publication is Chemical Communications (Cambridge, United Kingdom) (2016), 52(43), 7009-7012, database is CAplus and MEDLINE.

A new synthetic approach to arylboronic esters from arylzinc reagents with boryl electrophiles MeOB(OR)₂ was developed. Also, this protocol could be applied to the cyclization/borylation of alkynylaryl iodides to afford cyclized vinylboronic esters.

Chemical Communications (Cambridge, United Kingdom) 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

Hirota, Kosaku published the artcileNovel and efficient synthesis of 8-oxoadenine derivatives, Safety of 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Heterocycles (2001), 55(12), 2279-2282, database is CAplus.

A novel synthetic method for the preparation of 8-oxoadenine derivatives was reported. This widely applicable synthetic method was realized through the use of 5-amino-2,3-dihydro-2-oxo-1-(phenylmethyl)-1H-imidazole-4-carbonitrile as the key intermediates. A variety of substituents were successfully introduced to the 2- and 9-position of the 8-oxoadenine nucleus.

Heterocycles 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, Safety of 2-Aminomalononitrile 4-methylbenzenesulfonate.

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

Hirota, Kosaku published the artcileSynthesis and biological evaluation of 2,8-disubstituted 9-benzyladenines: discovery of 8-mercaptoadenines as potent interferon-inducers, COA of Formula: C10H11N3O3S, the publication is Bioorganic & Medicinal Chemistry (2003), 11(13), 2715-2722, database is CAplus and MEDLINE.

Recently, we have identified 9-benzyl-8-hydroxyadenines bearing an appropriate substituent (a butoxy, propylthio or butylamino group) at the 2-position as potent interferon (IFN)-inducers. Herein we report the design, synthesis, and IFN-inducing activity of 8-substituted 9-benzyladenines possessing such an appropriate substituent at the 2-position. Introduction of the appropriate substituent into the 2-position of the adenine nucleus gave rise to expression of the activity even in 9-benzyladenines bearing no hydroxyl group at the 8-position. An amino group at the 6-position and a hydroxyl or thiol group carrying an acidic proton at the 8-position are required to express excellent IFN-inducing activity. 9-Benzyl-2-butoxy-8-mercaptoadenine indicated the most potent activity with MEC of 0.001 μM.

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, COA of Formula: C10H11N3O3S.

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

Hirota, Kosaku published the artcileEfficient synthesis of 2,9-disubstituted 8-hydroxyadenine derivatives, Quality Control of 5098-14-6, the publication is Organic & Biomolecular Chemistry (2003), 1(8), 1354-1365, database is CAplus and MEDLINE.

An efficient and general method for the synthesis of 2,9-disubstituted 8-hydroxyadenines, e.g. I, which are expected to have various biol. activities, was realized. 5-Amino-4-cyano-2-hydroxyimidazoles, e.g. II, were prepared from aminomalononitrile and isocyanates as key intermediates. The condensation of II with amidines, imidates, guanidine, urea and thioureas afforded 8-hydroxyadenines, e.g. III, possessing various substituents at the 2-position. Furthermore, selective alkylation of 2-amino- and 2-hydroxyadenines (IV and V) successively proceeded to give the corresponding 2-alkylamino- and 2-alkoxyadenines, resp. 2-Alkylthioadenines, e.g. VI, were prepared by an analogous reaction of II with benzoyl isothiocyanate and subsequent S-alkylation. The imidazoles, e.g. II, are most useful intermediates for the synthesis of 8-hydroxyadenine derivatives

Organic & Biomolecular 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, Quality Control of 5098-14-6.

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

Melent’eva, T. A. published the artcilePolarographic reduction of hydrobromides of dipyrrylmethenes, Related Products of nitriles-buliding-blocks, the publication is Zhurnal Obshchei Khimii (1972), 42(10), 2274-9, database is CAplus.

In I (R = Me, Et, CO2Et, NO2, CN, Ac, CH2CO2H), prepared by heating 2-formyl-3-acetyl-4-methyl-5-carbethoxypyrrole and pyrroles unsubstituted in the 2-position in the presence of HBr, the polarog. curves show a linear relation between halfwave potentials and the substituent constants The transmission of the substituent effect in the β-position with respect to dipyrrolylmethene chromophore occurs mainly through resonance. MeCOCH2CO2Et in AcOH, treated with aqueous NaNO2 and AcOH, followed by Zn dust and Et levulinate, gave 10% 2,4-dimethyl-3-carbethoxymethyl-5-carbethoxypyrrole, which with aqueous alc. NaOH gave the free dicarboxylic acid. The latter was heated with ethanolamine at 150° to give 2,4-dimethyl-3-carboxymethylpyrrole in 50% yield.

Zhurnal Obshchei Khimii published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, Related Products of nitriles-buliding-blocks.

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

Kodama, Koichi published the artcileCyanative self-condensation of aromatic aldehydes promoted by VO(OⁱPr)₃-Lewis base as a cooperative catalyst, Application of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Organic & Biomolecular Chemistry (2012), 10(47), 9440-9446, database is CAplus and MEDLINE.

In the presence of oxovanadium triisopropoxide and an amine such as 4-dimethylaminopyridine, aromatic aldehydes underwent self-condensation with trimethylsilyl cyanide under an oxygen atm. in acetonitrile to give α-cyanobenzyl benzoates RCH(CN)OCOR (R = Ph, 2-ClC₆H₄, 3-ClC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, 4-MeC₆H₄, 2-MeOC₆H₄, 3-MeOC₆H₄, 4-MeOC₆H₄) (I) in 28-81% conversions and with 93:7-99:1 chemoselectivity for the cyanobenzyl benzoates over the corresponding cyanohydrins. A variety of Lewis base additives acted as cocatalysts for the reaction; reactions performed under nitrogen gave similar conversions but reduced selectivities for cyanobenzyl benzoates. The choice of solvent also altered chemoselectivity significantly. When (R)-PhCHMeNMe₂ was used as a Lewis basic cocatalyst, (S)-I (R = 4-ClC₆H₄) was obtained in 61% conversion, 99:1 chemoselectivity, and 8% ee.

Organic & Biomolecular 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, Application of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Tominaga, Yoshinori published the artcileSynthesis of 4-(methylthio)-2(1H)-pyridone derivatives using ketene dithio acetals, Quality Control of 57663-05-5, the publication is Journal of Heterocyclic Chemistry (1987), 24(5), 1325-31, database is CAplus.

Reaction of active methylene compounds with ketene dithioacetals, (MeS)₂C:C(CN)₂ and (MeS)₂C:C(CN)CONH₂ gave cyanomethylthiopyridone I [R = Me, CH₂CH₂CO₂H, (un)substituted Ph; R¹ = H, Me, Ac, CO₂Et, CH₂CO₂H; RR¹ = (CH₂)₄]. The transformation of 4-methylthiooxopyrancarbonitriles II (R² = Ph, C₆H₄Br-4, C₆H₄OMe-4, Me, styryl) into I was also described.

Journal of Heterocyclic Chemistry published new progress about 57663-05-5. 57663-05-5 belongs to nitriles-buliding-blocks, auxiliary class Fused/Partially Saturated Cycles,Tetrahydropyrimidins, name is 6-Methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile, and the molecular formula is C11H16BNO3, Quality Control of 57663-05-5.

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