Category: 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.

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

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

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

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

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

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

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

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

Steven, Alan published the artcileUse of a Curtius Rearrangement as Part of the Multikilogram Manufacture of a Pyrazine Building Block, Computed Properties of 5098-14-6, the publication is Organic Process Research & Development (2018), 22(1), 77-81, database is CAplus.

2-Amino-5-methylpyrazine I was prepared on multikilogram scale as an intermediate in the preparation of a glucokinase activator using the Curtius rearrangement of an acyl azide derived from 5-methyl-2-pyrazinecarboxylic acid as the key step. The formation of an acyl azide for the Curtius rearrangement required a process safety control strategy to be put in place. The process developed was used to successfully deliver multikilogram quantities of I in an overall yield of 68% starting from 5-methylpyrazine-2-carboxylic acid.

Organic Process Research & Development 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 C3H12Cl2N2, Computed Properties of 5098-14-6.

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

Barnathan, Gilles published the artcileSynthesis of C-nucleosides. XI. 2-D-Arabinofuranosylimidazoles and 8-D-arabinofuranosylpurines, Related Products of nitriles-buliding-blocks, the publication is European Journal of Medicinal Chemistry (1976), 11(1), 67-72, database is CAplus.

The nucleoside analogs I (R = NH2, SH, R1 = H) were prepared by treating II (R1 = R2 = Bz, R3 = Cl, Br) with Hg(CN)2, cleaving benzoyl groups from II (R1 = R2 = Bz, R3 = CN), treating II (R1 = Bz, R2 = H, R3 = CN) with PhCH2SH, cyclizing II (R1 = Bz, R2 = H, R3 = CH(:NH)SCH2Ph) with H2NCH(CN)2, cyclizing II (R1 = Bz, R2 =H, R3 = 4-cyano-5-amino-2-imidazolyl) with HC(:NH)NH2 or HC(OEt)3 and NaSH, and cleaving the benzoyl groups from I (R1 = Bz).

European Journal of 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, Related Products of nitriles-buliding-blocks.

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