Author: Jessica.F

Kadir, Kamaliah published the artcilePurines, pyrimidines, and imidazoles. Part 56. Some aminoimidazolecarboxamidines and derived adenines, Formula: C10H11N3O3S, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1980), 2728-31, database is CAplus.

Cyclohexylimidazole I, prepared (37%) from H₂NCH(CN)₂, CH(OEt)₃, and cyclohexylamine, gave 66% carboximidate II (R = OMe) on treatment with MeOH/HCl, which with NH₃ gave 64% carboxamidine II (R = NH₂) (III). Formylation of III gave N⁶-formyladenine IV (R = cyclohexyl), which was also prepared by formylation of 9-cyclohexyladenine. IV [R = CH₂CH(OH)CH₂OH] was similarly prepared The reaction of II (R = H) with HCO₂H/Ac₂O gave N⁶-formyladenine (IV; R = H), which was also prepared by formylation of adenine, whereas adenosine was not N-formylated under the same conditions.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) 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

He, Jian published the artcilePd(II)-Catalyzed Enantioselective C(sp³)-H Borylation, Category: nitriles-buliding-blocks, the publication is Journal of the American Chemical Society (2017), 139(9), 3344-3347, database is CAplus and MEDLINE.

Pd(II)-catalyzed enantioselective borylation of C(sp³)-H bonds has been realized for the first time using chiral acetyl-protected aminomethyl oxazoline ligands. This reaction is compatible with carbocyclic amides containing α-tertiary as well as α-quaternary carbon centers. The chiral β-borylated amides are useful synthons for the synthesis of chiral β-hydroxylated, β-fluorinated, and β-arylated carboxylic acids.

Journal of the American Chemical Society published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Category: nitriles-buliding-blocks.

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

Wang, Jian-Shu published the artcileAcOH-catalyzed aza-Michael addition/N-nitrosation: An efficient approach to CF₂HCH₂-containing N-nitrosoamines, Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Tetrahedron (2018), 74(28), 3904-3911, database is CAplus.

A simple and highly efficient protocol for the AcOH-catalyzed three-component reaction of nitroalkenes, difluoroethylamine and tert-Bu nitrite through cascade aza-Michael addition/N-nitrosation has been developed. A range of CF₂HCH₂-containing N-nitrosoamines were obtained in good to excellent yields. This approach features easily available cheap materials, without using addnl. organic solvents, simple operation under room temperature, gram scalable preparation and functionally diverse products.

Tetrahedron 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 C8H7N3, Name: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Wu, J.-M. published the artcileSynthesis and cytotoxicity of artemisinin derivatives containing cyanoarylmethyl group, Application In Synthesis of 13312-84-0, the publication is European Journal of Medicinal Chemistry (2001), 36(5), 469-479, database is CAplus and MEDLINE.

A series of 12α-deoxoartemisinyl cyanoarylmethyl dicarboxylates, dicarboxylic acids 12α-deoxoartemisinyl ester cyanoarylmethyl amide, and dicarboxylic acids 12α-deoxoartemisinyl ester N-methylcyanoarylmethyl amide, I (Y = (CH₂)₂, (CH₂)₄, (CH₂)₅, (CH₂)₇; X = O, NH, NMe) showing moderate cytotoxicity against P388 and L1210 cells were prepared They induced the significant accumulation of L1210 and P388 cells in the G1 phase of the cell cycle. This mechanism of action was quite different from that of the majority of cytotoxic compounds used in the chemotherapy of cancer. Compound I possessed better cytotoxicity than the other compounds

European Journal of Medicinal 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 C9H8BNO2, Application In Synthesis of 13312-84-0.

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

Guo, Xing-Tao published the artcileHighly enantioselective Michael addition of α,α-disubstituted aldehydes to nitroolefins, SDS of cas: 5153-73-1, the publication is Research on Chemical Intermediates (2016), 42(7), 6373-6380, database is CAplus.

A highly enantioselective Michael addition reaction of α,α-disubstituted aldehydes to β-nitrostyrenes has been developed. In the presence of rosin-based chiral primary amine-thiourea, γ-nitroaldehydes I [ Ar = 4-NO₂C₆H₄, 2-NO₂C₆H₄, 4-CNC₆H₄, 4-CF₃C₆H₄, 4-FC₆H₄, 2-furyl, etc.; R¹ = Me, Et; R² = Et, n-Pr, Ph, etc.; R¹= R² = (CH₂)₅] were afforded in excellent enantioselectivities (up to 99 % ee) with up to 99 % yield.

Research on Chemical Intermediates 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 C9H6N2O2, SDS of cas: 5153-73-1.

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

Ustinov, A. K. published the artcileSynthesis of γ-carbolines containing NO-donor fragment and assessment of their anticholinesterase activity, Category: nitriles-buliding-blocks, the publication is Russian Chemical Bulletin (2016), 65(11), 2718-2721, database is CAplus.

Hybrid γ-carboline-based compounds containing a nitrooxy group as an NO-donor were prepared It was shown that the introduction of this group did not affect the inhibitory activity of γ-carboline pharmacophore against acetyl- and butyrylcholinesterase.

Russian Chemical Bulletin 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 C5H5F3O2, Category: nitriles-buliding-blocks.

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

Francisco, Ma. Elena Y. published the artcileSynthesis and Structure-Activity Relationships of Amide and Hydrazide Analogues of the Cannabinoid CB₁ Receptor Antagonist N-(Piperidinyl)- 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716), Synthetic Route of 49540-34-3, the publication is Journal of Medicinal Chemistry (2002), 45(13), 2708-2719, database is CAplus and MEDLINE.

Analogs of the biaryl pyrazole N-(piperidinyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide, SR141716 (I) were synthesized to investigate the structure-activity relation (SAR) of the aminopiperidine region. The structural modifications include the substitution of alkyl hydrazines, amines, and hydroxyalkylamines of varying lengths for the aminopiperidinyl moiety. Proximity and steric requirements at the aminopiperidine region were probed by the synthesis of analogs that substitute alkyl hydrazines of increasing chain length and branching. The corresponding amide analogs were compared to the hydrazides to determine the effect of the second nitrogen on receptor binding affinity. The N-cyclohexyl amide (II) represents a direct methine for nitrogen substitution for I, reducing the potential for heteroatom interaction, while the morpholino analog adds the potential for an addnl. heteroatom interaction. The series of hydroxyalkyl amides of increasing chain length was synthesized to investigate the existence of addnl. receptor hydrogen binding sites. In displacement assays using the cannabinoid agonist [³H](1R,3R,4R)-3-[2-hydroxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-hydroxypropyl) cyclohexan-1-ol (CP 55 940) or the antagonist [³H]I,II exhibited the highest CB₁ affinity. In general, increasing the length and bulk of the substituent was associated with increased receptor affinity and efficacy (as measured in a GTP-γ-[³⁵S] assay). However, in most instances, receptor affinity and efficacy increases were no longer observed after a certain chain length was reached. A quant. SAR study was carried out to characterize the pharmacophoric requirements of the aminopiperidine region. This model indicates that ligands that exceed 3 Å in length would have reduced potency and affinity with respect to I and that substituents with a pos. charge d. in the aminopiperidine region would be predicted to possess increased pharmacol. activity.

Journal of Medicinal Chemistry published new progress about 49540-34-3. 49540-34-3 belongs to nitriles-buliding-blocks, auxiliary class Aliphatic Chain, name is Ethylhydrazine dihydrochloride, and the molecular formula is C2H10Cl2N2, Synthetic Route of 49540-34-3.

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

Gvozdyakova, A. published the artcileHydrazides of o-, m-, and p-substituted derivatives of α-hydroxyphenylacetic acid, Quality Control of 13312-84-0, the publication is Acta Facultatis Rerum Naturalium Universitatis Comenianae, Chimia (1966), 9(12), 585-94, database is CAplus.

The following cyanohydrins XC6H4CH(OH)CN (I) were prepared by treating 1.25 moles aldehyde and 1 mole KCN with 1 mole H2SO4 (as a 1:1 solution) at 10-20° (X, m.p. or b.p., and % yield given): H, b12-14 98-102°, 73.4; p-NO2, 197°, 45.0; o-NO2, 213-15°, 41.6; m-NO2, b12 183-7°, 36.4; p-Cl, 198-9°, 66.3; o-Cl, b18-20 165-70°, 62.1; o-OH, 148°, 69.9. The following Et α-hydroxyarylacetates XC6H4CH(OH)CO2Et (II) were prepared by heating 0.015 mole I with 3 ml. absolute EtOH and 3 ml. concentrated H2SO4 (X, m.p. or b.p., and % yield given): H, b12 60-4°, 73.7; p-NO2, 55-6°, 43.3; o-NO2, 134°, 35.2; m-NO2, 38.5°, 27.3; p-Cl, 172-4°, 71.6; o-Cl, b12 88-91°, 81.3; o-OH, 212-14°, 76.4. When 0.03 mole II was heated 4 hrs. with 10 ml. absolute EtOH and 6 ml. 50% H2NNH2.H2O, the product distilled in vacuo and the solid was recrystallized from EtOH, the following XC6H4CH(OH)CONHNH2 were prepared X, m.p., and % yield given): H, 91-2°, 75.9; p-NO2, 223-5°, 53.7; o-NO2, 239°, 37.4; m-NO2, 156-7°, 76.2; p-Cl, 90-2°, 54.05; o-Cl, 174-5°, 71.7; o-OH, 260-2°, 54.3. The hydrazides had no inhibitory effect, even at high concentration, on tubercular bacilli.

Acta Facultatis Rerum Naturalium Universitatis Comenianae, Chimia 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

Huang, Shengying published the artcileAsymmetric sequential double Michael reactions of γ,δ-unsaturated β-ketoesters to nitroolefins catalyzed by Ni (II)-diamine complex, HPLC of Formula: 5153-73-1, the publication is Catalysis Communications (2017), 67-70, database is CAplus.

The asym. sequential double Michael reactions of γ,δ-unsaturated β-ketoesters and nitroolefins catalyzed by 2 mol% of readily prepared Ni(II)-bis[(R,R)-N,N’-dibenzylcyclohexane-1,2-diamine] complex and then with 1 equiv of tetramethylguanidine (TMG) for cyclization have been developed. The reaction gave the corresponding Michael adducts of multifunctional cyclohexenol derivatives with three chiral stereocenters in good yields, moderate diastereoselectivities, and high enantioselectivities under mild reaction conditions. Thus, e.g., γ,δ-unsaturated β-ketoester I + trans-β-nitrostyrene â†?II (82%, dr = 5:1, 92% ee).

Catalysis Communications 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 C9H6N2O2, HPLC of Formula: 5153-73-1.

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

Hamzehloueian, Mahshid published the artcileAn experimental and theoretical study on the regioselective synthesis of a new class of spiropyrrolothiazoles with quinoxaline motifs via a 1,3-dipolar cycloaddition reaction. An evaluation of DFT methods, Quality Control of 5153-73-1, the publication is RSC Advances (2015), 5(93), 76368-76376, database is CAplus.

A series of novel spiropyrrolothiazoles I (R = Ph, 4-MeC₆H₄, 2-O₂NC₆H₄, 2-furyl, 2-thienyl, 1-naphthyl, etc.) with quinoxaline motifs was synthesized by a four-component 1,3-dipolar cycloaddition reaction of various trans-β-nitroalkenes RCH:CHNO₂ and an azomethine ylide, generated in situ from 1,3-thiazolidine-4-carboxylic acid, ninhydrin and 1,2-phenylenediamine. The stereochem. of the products was confirmed by single crystal X-ray structure and spectroscopic techniques. Theor. calculations were carried out using DFT methods at the B3LYP/6-31G(d,p), wB97xD/6-31G(d,p) and M06-2X/6-31G(d,p) levels. The regio- and stereoselectivity was explained on the basis of transition state stabilities and global and local reactivity indexes of the reactants. The assessment of geometries and energetics of transition states revealed the importance of π/π interactions between aromatic rings in the regioselectivity of the cycloaddition reaction. The B3LYP functional was unable to deal with this weak interaction in the proposed TSs and led to an incorrect conclusion about the reaction regioselectivity. In this report, wB97xD and M06-2X functionals to calculate the transition states relative energies were successfully employed.

RSC Advances 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 C9H6N2O2, Quality Control of 5153-73-1.

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