Month: December 2022

Tam Huynh Dinh published the artcileSynthesis of C-nucleosides. VII. β-D-Ribofuranosyl-2- and -8-adenines, Related Products of nitriles-buliding-blocks, the publication is Journal of Heterocyclic Chemistry (1975), 12(1), 111-17, database is CAplus.

Benzyl (O-benzoyl-5-D-ribofuranosyl)thioformimidate reacted with aminomalodinitrile or with 5-amino-4-cyanoimidazole to yield the two C-nucleoside analogs I and II of adenosine. The β-configuration was determined with NMR and CD spectra.

Journal of Heterocyclic 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 C9H9BrO2, Related Products of nitriles-buliding-blocks.

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

Van Genderen, H. published the artcileToxicological properties of the herbicide dichlobenil, 2,6-dichlorobenzonitrile, in warm-blooded animals, SDS of cas: 3336-34-3, the publication is Mededelingen Rijksfaculteit Landbouwwetenschappen, Gent (1966), 31(3), 1026-31, database is CAplus.

After oral administration of 100 mg. dichlobenil/kg. body weight, rabbits converted approx. 23% into 2,6-dichloro-3-hydroxybenzonitrile (I) and 2% into the 4-hydroxy analog (II). Rats excreted, resp., 22% and 9% of I and II. In mice the i.p. LD50 for I and II was 83 mg./kg. and 50 mg./kg., resp. The oral toxicity for mice and rabbits was very much lower. The effects of I and II were studied on the respiration of bakers’ yeast, on the ATPase induction in isolated mitochondria, on the contraction of isolated rat diaphragm, and on single beating rat heart cells in tissue culture. It was concluded that I and II, like other chlorophenols, were uncoupling agents of oxidative phosphorylation with approx. the same potency as 2,4-dinitrophenol. Liver function tests with dichlobenil showed different results for rats and rabbits. The effect on the liver of the rat seemed to be reversible, but, at a critical dose level for the rabbit, it was irreversible. It was suggested that in the rat liver cells the conjugation of the phenols to glucuronides and sulfates could keep pace with their formation.

Mededelingen Rijksfaculteit Landbouwwetenschappen, Gent published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C8H10S, SDS of cas: 3336-34-3.

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

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

Noe, Christian R. published the artcileChiral lactols. XIII. On the determination of the absolute configuration of aromatic cyanohydrins and structurally related compounds, Quality Control of 13312-84-0, the publication is Liebigs Annalen (1995), 1353-60, database is CAplus.

Synthesis and conformational anal. of diastereomeric acetals, e.g. I, of aromatic cyanohydrins and structurally related compounds are described. Based on ¹H-NMR spectroscopic and x-ray data it is shown that the absolute configuration of such compounds can be assigned according to a method, which has been presented previously for secondary arylalkyl alcs.

Liebigs Annalen 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, Quality Control of 13312-84-0.

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

Noe, C. R. published the artcileAmino alcohols. II: Preparation of enantiomerically pure pharmacologically active β-amino alcohols, Computed Properties of 13312-84-0, the publication is Monatshefte fuer Chemie (1995), 126(4), 481-94, database is CAplus.

A synthesis of β-amino alcs. is described starting from racemic or enantiomerically pure α-hydroxynitriles which were O-protected using enantiomerically pure acetal type protective groups. Reduction with lithium aluminum hydride yielded O-protected β-amino alcs. Whenever diastereomeric O-protected cyanohydrins could not be separated, the mixture was reduced and the resulting O-protected amino alcs. were separated Removal of the protective group using hydrogen chloride and methanol yielded enantiomerically pure β-amino alcs. or their corresponding hydrochlorides. For example, the chiral synthesis of (R)-1-amino-3-(1-naphthalenyloxy)-2-propanol and (S)-1-amino-3-(1-naphthalenyloxy)-2-propanol was accomplished via resolution of (±)-2-hydroxy-3-(1-naphthalenyloxy)propanenitrile.

Monatshefte fuer Chemie 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, Computed Properties of 13312-84-0.

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

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.

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.

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

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.

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.

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