Tag: 100-200

Heterogeneous Gold-Catalyzed Cascade Hydrogen-Transfer Strategy for Selective Synthesis of Quinazolinones in Water was written by Tang, Lin;Zhao, Xianghua;Zou, Guodong;Zhou, Yuqiang;Yang, Xingkun. And the article was included in Asian Journal of Organic Chemistry in 2016.Application In Synthesis of 5-Methyl-2-nitrobenzonitrile This article mentions the following:

Efficient and selective synthesis of quinazolinones from 2-nitrobenzonitriles and benzylic alcs. catalyzed by TiO₂-supported gold nanoparticles (Au/TiO₂) was developed. Various transformations, such as dehydrogenative oxidation of C-O and C-N bonds, reduction of nitro groups, condensation of aldehydes with amines, hydration of cyano groups and cyclization, was achieved in the tandem hydrogen-transfer reaction. This protocol presents broad substrate scope, good tolerance to air and water, excellent recycling of the catalyst and did not require any additive, oxidant or reductant, which enables straightforward, practical and environmentally benign C-N and C-O bond formation. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Application In Synthesis of 5-Methyl-2-nitrobenzonitrile).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Application In Synthesis of 5-Methyl-2-nitrobenzonitrile

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Thermal chlorination of n-heptane was written by Galanina, R. S.. And the article was included in Doklady Akademii Nauk SSSR in 1953.Computed Properties of C7H11NO This article mentions the following:

Continuous thermal chlorination of n-C₇H₁₆ was studied in a continuous-flow apparatus (cf. first reference above) with rapid removal of RCl from the reaction zone. With a ratio RH:Cl₂ of 10:1 at 0.73 space velocity 50% RCl with only a trace of dichlorides is formed at 180°. At higher temperatures the yield of RCl rises and the dichloride disappears. At 260° is obtained the best yield, 96.5% RCl. At this temperature the yield of RCl rises steadily as the RH:Cl₂ ratio is increased although both 8:1 and 10:1 ratios give the same high yield of 96.5%. Fractionation of the RCl gave 2 fractions, b. 134-6° and b. 147-50°, corresponding, resp., to 2-and 1-chloroheptane, identified further by d. and n. No tertiary halides were found, showing there is no isomerization of RH. At the temperature employed, the rate of substitution of primary H is greater than that of the secondary H atoms, but at lower temperatures the reverse is true. Chlorination of the crude RCl was run to obtain the dichlorides; with a 6:1 ratio of RCl: Cl₂ at 0.45 space velocity of Cl₂, the yield of dichlorides was 79.7% at 240°, 90% at 260°, and 99.2% at 280°. Fractionation gave 1,7-, 1,1- and 1,2-dichloroheptanes. Only at 220-40° does equilibrium exist in the rates of replacement of primary and secondary H atoms by Cl, while at 260° the highest rate of primary H replacement occurs (cf. Nekrasova, C.A. 48, 2560d, for chlorination in the liquid phase). The yields and properties of the isomeric dichlorides follow: 1,1, 31.5%, b₂₀ 82°, d₂₀ 1.0088, n²⁰_D 1.4440; 1,2, 15%, b₇ 68-72°, d₂₀ 1.0625, n²⁰_D 1.4480; 1,7, 53.1%, b₂₈ 120°, d₂₀ 1.048, n²⁰_D 1.4500. In the experiment, the researchers used many compounds, for example, 4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6Computed Properties of C7H11NO).

4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Computed Properties of C7H11NO

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KG-60-piperazine as a new heterogeneous catalyst for Gewald three-component reaction was written by Rezaei-Seresht, Esmail;Tayebee, Reza;Yasemi, Mohammad. And the article was included in Synthetic Communications in 2013.Category: nitriles-buliding-blocks This article mentions the following:

Piperazine supported on amorphous silica (KG-60-piperazine) as a basic catalyst acts in the Gewald three-component reaction of some aldehydes and ketones with malononitrile as well as Et cyanoacetate. The catalyst shows general utility with a variety of starting carbonyl compounds Moreover, the catalyst can be reused for four addnl. cycles without significant loss of the activity. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Category: nitriles-buliding-blocks).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Category: nitriles-buliding-blocks

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Design, synthesis, and biological evaluation of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinones as a new series of AMPKα1β1γ1 activators was written by Xiao, Zhihong;Peng, Yajun;Zheng, Bifeng;Chang, Qi;Guo, Yating;Chen, Zhuo;Li, Qianbin;Hu, Gaoyun. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2021.Name: 2-(Trifluoromethoxy)benzonitrile This article mentions the following:

Three series of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinone derivatives I [R¹ = 2-Me, 3-OMe, 4-F, etc.; R² = CF₃, COOH; R³ = H, 4-methoxybenzyl; R⁴ = H, 4-methoxybenzyl] were synthesized and reported as AMPKα1β1γ1 activators. The in vitro biol. assay demonstrated that compounds I [R¹ = 4-Cl; R² = CF3; R³ = H; R⁴ = H] (EC₅₀[AMPKα1γ1β1] = 180 nM) and I [R¹ = 3-CF₃; R² = COOH; R³ = H; R⁴ = H] (EC₅₀[AMPKα1γ1β1] = 2 nM) displayed significant enzyme activation. Mechanism studies indicated that both compounds reduced the levels of reactive oxygen species in a rat kidney fibroblast cell line (NRK-49F) stimulated by transforming growth factor-β and induced early apoptosis of NRK-49F cells at 10μM. Mol. docking studies suggested that compoundI [R¹ = 3-CF₃; R² = COOH; R³ = H; R⁴ = H] exhibited critical hydrogen-bond interactions with the critical amino acid residues Lys29, Lys31, Asn111, and Asp88 at the binding site of the AMPK protein. These results enriched the structure pool of AMPK activators and provided novel lead compounds for the subsequent development of compounds with a promising therapeutic potential against DN. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4Name: 2-(Trifluoromethoxy)benzonitrile).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Name: 2-(Trifluoromethoxy)benzonitrile

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Nitrile – Wikipedia,
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Synthesis of 5-substituted tetrazoles via DNA-conjugated nitrile was written by Du, Huang-Chi;Matzuk, Martin M.;Chen, Ying-Chu. And the article was included in Organic & Biomolecular Chemistry in 2020.Related Products of 60979-25-1 This article mentions the following:

A zinc bromide-catalyzed synthesis of 5-substituted tetrazoles via DNA-conjugated nitriles using sodium azide has been developed. The protocol offered moderate to excellent yields of tetrazoles with a broad range of substrates, including a variety of functionalized aromatic, heterocyclic, and aliphatic nitriles. In addition, the electronic effect within the substrate scope was evaluated. DNA fidelity was assessed by ligation efficiency and amplifiability anal. The ability to generate tetrazoles expands the diversity of heterocycles in the preparation of DNA-encoded chem. libraries. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Related Products of 60979-25-1).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Related Products of 60979-25-1

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Nitrile – Wikipedia,
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Synthesis and pharmacological evaluation of imidazoline sites I₁ and I₂ selective ligands was written by Anastassiadou, Maria;Danoun, Saida;Crane, Louis;Baziard-Mouysset, Genevieve;Payard, Marc;Caignard, Daniel-Henri;Rettori, Marie-Claire;Renard, Pierre. And the article was included in Bioorganic & Medicinal Chemistry in 2001.Reference of 55406-13-8 This article mentions the following:

Several series of 2-aryl or 2-heterocyclic-imidazoline derivatives have been prepared and evaluated in vitro as ligands for imidazoline (I₁ and I₂) and α-adrenergic (α₁ and α₂) receptors. Their pK_i values indicate that linkage of the imidazoline moiety at the 2-position with an aromatic substituent dramatically decreases α-adrenergic affinity. I₁ sites are more accessible by Ph imidazolines substituted by a Me or a methoxy group at the ortho or meta position. Indeed, 2-(2′-methoxyphenyl)-imidazoline is one of the best I₁ ligands ever reported (pK_i = 8.53 and I₁/I₂ > 3388). On the other hand, I₂ selectivity increases in the presence of a Me group in the para position. The original compound, 2-(3′-fluoro-4′-tolyl)-imidazoline, is a new potent ligand for the I₂ sites with high selectivity (pK_i = 8.53 and I₂/I₁ > 3388). In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Reference of 55406-13-8).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Reference of 55406-13-8

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Nitrile – Wikipedia,
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Structure-activity relationships of novel potent MurF inhibitors was written by Gu, Yu Gui;Florjancic, Alan S.;Clark, Richard F.;Zhang, Tianyuan;Cooper, Curt S.;Anderson, David D.;Lerner, Claude G.;McCall, J. Owen;Cai, Yingna;Black-Schaefer, Candace L.;Stamper, Geoffrey F.;Hajduk, Philip J.;Beutel, Bruce A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2004.Related Products of 70291-62-2 This article mentions the following:

A novel class of MurF inhibitors was discovered and structure-activity relationship studies have led to several potent compounds with IC₅₀ = 22 ∼ 70 nM. Unfortunately, none of these potent MurF inhibitors exhibited significant antibacterial activity even in the presence of bacterial cell permeabilizers. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Related Products of 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Related Products of 70291-62-2

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Nitrile – Wikipedia,
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2,4,6-Triaminopyrimidine as a Novel Hinge Binder in a Series of PI3Kδ Selective Inhibitors was written by Patel, Leena;Chandrasekhar, Jayaraman;Evarts, Jerry;Haran, Aaron C.;Ip, Carmen;Kaplan, Joshua A.;Kim, Musong;Koditek, David;Lad, Latesh;Lepist, Eve-Irene;McGrath, Mary E.;Novikov, Nikolai;Perreault, Stephane;Puri, Kamal D.;Somoza, John R.;Steiner, Bart H.;Stevens, Kirk L.;Therrien, Joseph;Treiberg, Jennifer;Villasenor, Armando G.;Yeung, Arthur;Phillips, Gary. And the article was included in Journal of Medicinal Chemistry in 2016.Recommanded Product: 2-Amino-4,6-dichloropyrimidine-5-carbonitrile This article mentions the following:

Inhibition of phosphoinositide 3-kinase δ (PI3Kδ) is an appealing target for several hematol. malignancies and inflammatory diseases. Herein, we describe the discovery and optimization of a series of propeller shaped PI3Kδ inhibitors comprising a novel triaminopyrimidine hinge binder. Combinations of electronic and structural strategies were employed to mitigate aldehyde oxidase mediated metabolism This medicinal chem. effort culminated in the identification of 52, a potent and highly selective inhibitor of PI3Kδ that demonstrates efficacy in a rat model of arthritis. In the experiment, the researchers used many compounds, for example, 2-Amino-4,6-dichloropyrimidine-5-carbonitrile (cas: 1277179-33-5Recommanded Product: 2-Amino-4,6-dichloropyrimidine-5-carbonitrile).

2-Amino-4,6-dichloropyrimidine-5-carbonitrile (cas: 1277179-33-5) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Recommanded Product: 2-Amino-4,6-dichloropyrimidine-5-carbonitrile

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Base strengths of cyanoamines was written by Stevenson, Geo. W.;Williamson, Dallas. And the article was included in Journal of the American Chemical Society in 1958.Product Details of 7528-78-1 This article mentions the following:

Conjugate acids of cyanoamines have the following pK_a: Et₂NCN -2.0 ± 0.3, Et₂NCH₂CN 4.55, Et₂N(CH₂)₂CN 7.65, Et₂N(CH₂)₃CN 9.29, Et₂N(CH₂)₄CN 10.08, Et₂N(CH₂)₅CN 10.46, Et₂NCMe₂CN 9.13, HN(CH₂CN)₂ 0.2 ± 0.1, EtN(CH₂CN)₂ -0.6 ± 0.1, HN(CH₂CH₂CN)₂ 5.26, EtN(CH₂CH₂CN)₂ 4.55, N(CH₂CH₂CN)₃ 1.1 ± 0.1, H₂NCH₂CN 5.34, piperidinoacetonitrile 4.55, α-piperidinoisobutyronitrile 9.22, β-(N-amphetamine)propionitrile 7.23, β-(N-methamphetamine)propionitrile 6.95, and β-(N-norcodeine)propionitrile 5.68. The cyano group has a base-weakening effect attributed to inductive and field effects. Hall’s equations (C.A. 52, 1735f) were used to estimate σ^* values for the cyanoalkyl groups. pK_a was determined by potentiometric titration of the strong bases with HCl or of salts of weaker bases with NaOH. For the very weak bases titration curves were determined spectrophotometrically at 210 mμ, the bases showing considerable absorption at this wave length and the salts very little. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Product Details of 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Product Details of 7528-78-1

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Nitrile – Wikipedia,
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Epiphyseal plate lesions, degenerative arthritis, and dissecting aneurysms of the aorta produced by aminonitriles was written by Wawzonek, S.;Ponseti, I. V.;Shepard, R. S.;Wiedenmann, L. G.. And the article was included in Science (Washington, DC, United States) in 1955.Formula: C9H12N4 This article mentions the following:

β-Aminopropionitrile (I) fed to weanling rats at concentrations of 0.1, 0.4, and 1.0% in their diet produced widening and extensive disruption of the epiphyseal plates, widespread periosteal new bone formations, loosening and detachment of the ligamentous and tendinous insertions, degenerative arthritis, and dissecting aneurysms of the aorta. The severity of the epiphyseal plate lesions and periosteal new bone formation was in direct proportion to the concentration administered. Histologically these lesions appeared to be identical to the lesions observed in rats fed diets containing 50% Lathyrus odoratus seeds (cf. Federation Proc. 13, 473(1954)). Following the method of Dupuy and Lee (C.A. 48, 4182h) the compound β-(γ-L-glutamylamino)propionitrile was isolated from these germinating seeds and found to be active in producing the skeletal lesions when fed at a 1% level. In order to determine the active moiety of this compound weanling rats were fed the following diet: 1% β-alanine plus 1% L-glutamic acid, 1 and 2% propionitrile, 1 and 2% acetonitrile, 1% indoleacetonitrile, 0.4 and 1% bis(2-cyanoethyl)amine (II); 0.4 and 1% tris(2-cyanoethyl)amine, and 0.1, 0.4, and 1% I. Only II produced death (1% concentration for 16 days), or skeletal lesions (0.4% concentration for 50 days). In order to determine the mode of action of I, weanling rats were fed 0.1 and 0.4% acrylonitrile and were injected subcutaneously with sublethal doses of KCN. Neither of these produced skeletal lesions. Investigators of other aminonitriles revealed that aminoacetonitrile at the 0.2% level produced extremely severe skeletal lesions 2 weeks after feeding, and at the 1% level killed within 6 days. α-Aminopropionitrile at 1.0 and 0.2% levels stunted the rats but did not produce detectable skeletal lesions. γ-Aminobutyronitrile (0.2% level) had no abnormal effect. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Formula: C9H12N4).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Formula: C9H12N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts