Tag: M.W=250-300

Taylor, Edward C. published the artcilePteridines. XXXII. 2-Amino-3-cyano-5-chloromethylpyrazine 1-oxide and its conversion to 6-alkenyl-substituted pteridines, HPLC of Formula: 5098-14-6, the publication is Journal of Organic Chemistry (1973), 38(16), 2817-21, database is CAplus.

2-Amino-3-cyano-5-chloromethylpyrazine 1-oxide (I), prepared by the condensation of β-chloropyruvaldoxime with aminomalononitrile tosylate, was deoxygenated with PCl3 to 2-amino-3-cyano-5-chloromethylpyrazine (II). Both I and II were converted by conventional procedures to triphenylphosphonium ylides (Wittig reagents) and, hence, by condensation with aldehydes, to parallel series of 5-alkenylpyrazines (III and IV). Cyclization of IV with guanidine gave 2,4-diamino-6-alkenylpteridines, of interest as intermediates for the synthesis of biopterin and biopterin analogs. Some addnl. reactions of the above pyrazine intermediates are also described.

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 C10H16O2, HPLC of Formula: 5098-14-6.

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

Taylor, Edward C. published the artcilePteridines. XXXIX. Synthesis of 2,4-diamino-7-alkenylpteridines and their 8-oxides, Product Details of C10H11N3O3S, the publication is Journal of Organic Chemistry (1976), 41(8), 1299-303, database is CAplus.

A versatile and flexible route to a variety of 2,4-diamino-7-alkenylpteridines was described. Condensation of aminomalononitrile with α-oximino-β-chloroaldehydes R1COC(:NOH)CClR2R3 [R1-R3 = H; R1 = R2 = H, R3 = Me, Pr; R1R2 = (CH2)3, R3 = H] (prepared by the addition of nitrosyl chloride to α,β-unsaturated aldehydes) gave 2-amino-3-cyano-6-(1-chloroalkyl)pyrazine 1-oxides I. The 6-chloromethyl compound I (R1-R3 = H) was converted to a stable phosphorane which was condensed with aldehydes to give a series of 2-amino-3-cyano-6-alkenylpyrazine 1-oxides II (R = Me, CH2OH, CO2H, Ph, 3,4-Cl2C6H3, 3,4-(OCH2O)C6H3, 2-thienyl, 3-pyridyl) which were cyclized with guanidine to 2,4-diamino-7-alkenylpteridine 8-oxides III (n = 1). Deoxygenation of I (R1-R3 = H) with PCl3 in THF gave 2-amino-3-cyano-6-chloromethylpyrazine, which analogously gave a series of 2,4-diamino-7-alkenylpteridines III (n = 0).

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 C21H24O8, Product Details of C10H11N3O3S.

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

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

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

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

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