Category: nitriles-buliding-blocks

“On-Water” Palladium-Catalyzed Tandem Cyclization Reaction for the Synthesis of Biologically Relevant 4-Arylquinazolines was written by Yuan, Shuo;Yu, Bin;Liu, Hong-Min. And the article was included in Chemistry – A European Journal in 2019.Safety of 2-Amino-3,5-dibromobenzonitrile This article mentions the following:

The quinazoline scaffold is prevalent in pharmaceutically relevant mols. that show diverse biol. activities. An efficient “on-water” palladium-catalyzed tandem cyclization reaction from com. available arylboronic acids RB(OH)₂ (R = Ph, 3-nitrophenyl, naphthalen-1-yl, etc.) and benzonitriles (E)-2-CN-R¹C₆H₄N=C(R²)N(Me)₂ [R¹ = H, 5-Me, 4,5-(OMe)₂, etc.; R² = H, Me] that enable the rapid access to 4-arylquinazoline scaffolds I [R³ = H, 7-Me, 6,7-(OMe)₂, etc.] in good to excellent yields (45 examples, up to 98% yield) was reported. This protocol has shown good functional group tolerance and broad substrate scope. The reaction was also performed on a gram scale and successfully applied to the synthesis of the highly potent and selective PI3Kδ inhibitor II, showing the practicability and synthetic utility of the protocol. In this reaction, the quinazoline scaffold I is efficiently constructed with the simultaneous formation of one C-C bond and one C-N bond. Collectively, the protocol could serve as an alternative strategy to synthesize biol. important quinazoline scaffolds. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Safety of 2-Amino-3,5-dibromobenzonitrile).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. 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.Safety of 2-Amino-3,5-dibromobenzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

ZrCl₄/[bmim]BF₄-Catalyzed condensation of salicylaldehydes and malononitrile: Single-step synthesis of 3-cyanocoumarin derivatives was written by Valizadeh, Hassan;Mahmoodian, Manzar;Gholipour, Hamid. And the article was included in Journal of Heterocyclic Chemistry in 2011.Computed Properties of C14H14N2O2 This article mentions the following:

A versatile and efficient single-step route to 3-cyanocoumarins via Knoevenagel condensation of salicylaldehydes and malononitrile using ZrCl₄ as the catalyst (15 mol %) in ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate as reaction medium and catalyst is described. The novel procedure features single step, short reaction time, good yields, and simple workup. J. Heterocyclic Chem., (2011). In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Computed Properties of C14H14N2O2).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Computed Properties of C14H14N2O2

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Nitrile – Wikipedia,
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Base-promoted N-alkylation using formamides as the N-sources in neat water was written by Chen, Wen-Xin;Zhang, Cai-Yun;Shao, Li-Xiong. And the article was included in Tetrahedron in 2014.Related Products of 37812-51-4 This article mentions the following:

An efficient catalyst-free, alternative method for the C-N bond formation reaction of alkyl electrophiles using formamides as the N-sources was achieved under mild conditions. The reaction possesses the advantages of a broad range of substrates scope and wide functional group tolerance. It should also be noted that this process was performed using the environmentally benign water as the sole solvent, and high yield can also be achieved in ten-gram scale. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Related Products of 37812-51-4).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) 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. 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.Related Products of 37812-51-4

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates was written by Wolfe, John P.;Tomori, Hiroshi;Sadighi, Joseph P.;Yin, Jingjun;Buchwald, Stephen L.. And the article was included in Journal of Organic Chemistry in 2000.Electric Literature of C14H12N2 This article mentions the following:

Palladium complexes supported by (2-PhC₆H₄)P(CMe₃)₂ (I) or (2-PhC₆H₄)PCy₂ (II; Cy = cyclohexyl) are efficient catalysts for the catalytic amination of a wide variety of aryl halides and triflates. Use of ligand I allows for the room-temperature catalytic amination of many aryl chloride, bromide, and triflate substrates, while ligand II is effective for the amination of functionalized substrates or reactions of acyclic secondary amines. The catalysts perform well for a large number of different substrate combinations at 80-110°, including chloropyridines and functionalized aryl halides and triflates using 0.5-1.0 mol% Pd; some reactions proceed efficiently at low catalyst levels (0.05 mol% Pd). These ligands are effective for almost all substrate combinations that have been previously reported with various other ligands, and they represent the most generally effective catalyst system reported to date. I and II are air-stable, crystalline solids that are com. available. Their effectiveness is due to a combination of steric and electronic properties that promote oxidative addition, Pd-N bond formation, and reductive elimination. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Electric Literature of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. 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.Electric Literature of C14H12N2

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Nitrile – Wikipedia,
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General Reductive Amination of Aldehydes and Ketones with Amines and Nitroaromatics under H₂ by Recyclable Iridium Catalysts was written by Sui, Dejun;Mao, Fei;Fan, Haipeng;Qi, Zhengliang;Huang, Jun. And the article was included in Chinese Journal of Chemistry in 2017.Computed Properties of C14H12N2 This article mentions the following:

Heterogeneous iridium catalysts were prepared and applied for the reductive amination of aldehydes and ketones with nitroaroms. and amines using H₂. The iridium catalysts were prepared by pyrolysis of ionic liquid 1-methyl-3-cyanomethylimidazoulium chloride ([MCNI]Cl) with iridium chloride (IrCl₃) in activated carbons. Iridium particles were well dispersed and stable in the N-doped carbon materials from [MCNI]Cl with activated carbon. The Ir@NC(600-2h) catalyst was found to be highly active and selective for the reductive amination of aldehydes and ketones using H₂ and a variety of nitrobenzenes and amines were selectively converted into the corresponding secondary and tertiary amines. The Ir@NC(600-2h) catalyst was reusable several times without evident deactivation. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Computed Properties of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Computed Properties of C14H12N2

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Nitrile – Wikipedia,
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Trigonal-Bipyramidal Copper(II) Complexes with Symmetric and Unsymmetric Tripodal Tetramine Ligands was written by Dittler-Klingemann, Andreas M.;Hahn, F. Ekkehardt. And the article was included in Inorganic Chemistry in 1996.Quality Control of 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

The syntheses of the aliphatic tripodal tetramine ligands N(CH₂CH₂CH₂NH₂)₃ (1), N[(CH₂CH₂CH₂NH₂)₂(CH₂CH₂NH₂)] (2), and N[(CH₂CH₂CH₂NH₂)(CH₂CH₂NH₂)₂] (3) are reported. The tripodal N₄– ligands 1–3 react with Cu(OH)₂ in H₂O to give blue Cu(II) complexes. Addition of NH₄PF₆ to such solutions yields [Cu(N₄)(NH₃)](PF₆)₂ [4; N₄ = 1, 4a; N₄ = 2, 4b; N₄ = 3, 4c]. The mol. structures of complexes 4a–c were determined by x-ray diffraction. All three complexes can be crystallized from H₂O. Selected crystallog. details are as follows 4a [4b] {4c}: formula C₉H₂₇CuF₁₂N₅P₂ [C₈H₂₅CuF₁₂N₅P₂] {C₇H₂₃CuF₁₂N₅P₂}, M = 558.82 [544.79] MLL {530.76} amu, monoclinic [monoclinic] {orthorhombic}, space group P2₁/c [C2/c] {P2₁2₁2}, a = 8.9519(14) [30.181(6)] {15.075(5)} Å, b = 16.803(3) [8.914(3)] {12.2939(14)} Å, c 13.834(2) [14.253(4)] {10.064(2)} , β = 94.183(12) [93.76(2)] {90.0}°, V = 2075.3(10) [3826(3)] {1865.2(12)} ų, Z = 4 [8] {4}, R = 5.10 [3.42] {4.32}, R_w = 6.67 [5.12] {5.23} for 2480 [2137] {1533} absorption corrected structure factors F_o² â‰?3σ(F_o²) and 262 [255] {245} refined parameters. The complex dications in 4a–c exhibit a trigonal-bipyramidal geometry with the tertiary N of the tripodal ligand and the NH₃ N in the axial positions. Complexes with the unsym. ligands 2 and 3 possess both five and six membered chelate rings. Depending on the ligand, the size of the cavity for the NH₃ ligand increases from 4a to 4c. This leads to a shortening of the Cu-NH₃ bond length with the shortest bond of this type observed for 4c. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Quality Control of 3,3′,3”-Nitrilotripropanenitrile).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Quality Control of 3,3′,3”-Nitrilotripropanenitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

2-(2-Thienyl)-5,6-dihydroxy-4-carboxypyrimidines as Inhibitors of the Hepatitis C Virus NS5B Polymerase: Discovery, SAR, Modeling, and Mutagenesis was written by Koch, Uwe;Attenni, Barbara;Malancona, Savina;Colarusso, Stefania;Conte, Immacolata;Di Filippo, Marcello;Harper, Steven;Pacini, Barbara;Giomini, Claudia;Thomas, Steven;Incitti, Ilario;Tomei, Licia;De Francesco, Raffaele;Altamura, Sergio;Matassa, Victor G.;Narjes, Frank. And the article was included in Journal of Medicinal Chemistry in 2006.Recommanded Product: 42137-24-6 This article mentions the following:

Infections caused by hepatitis C virus (HCV) are a significant world health problem for which novel therapies are in urgent demand. The polymerase of HCV is responsible for the replication of viral RNA. The authors recently disclosed dihydroxypyrimidine carboxylates as novel, reversible inhibitors of the HCV NS5B polymerase. This series was further developed into 5,6-dihydroxy-2-(2-thienyl)pyrimidine-4-carboxylic acids such as (I) (EC₅₀ 9.3 μM), which now show activity in the cell-based HCV replication assay. The structure-activity relation of these inhibitors is discussed in the context of their physicochem. properties and of the polymerase crystal structure. We also report the results of mutagenesis experiments which support the proposed binding model, which involves pyrophosphate-like chelation of the active site Mg ions. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Recommanded Product: 42137-24-6).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) 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. 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: 42137-24-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Palladium-Catalyzed Late-Stage Direct Arene Cyanation was written by Zhao, Da;Xu, Peng;Ritter, Tobias. And the article was included in Chem in 2019.Recommanded Product: 3-(tert-Butyl)benzonitrile This article mentions the following:

The first general late-stage aryl C-H cyanation with broad substrate scope and functional-group tolerance was reported. The reaction was enabled by a dual-ligand combination of quinoxaline and an amino acid-derived ligand. The method was applicable to direct cyanation of several marketed small-mol. drugs, common pharmacophores and organic dyes. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Recommanded Product: 3-(tert-Butyl)benzonitrile).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. 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.Recommanded Product: 3-(tert-Butyl)benzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of prenylated benzaldehydes and their use in the synthesis of analogs of licochalcone A was written by Kromann, Hasse;Larsen, Mogens;Boesen, Thomas;Schonning, Kristian;Nielsen, Simon Feldbaek. And the article was included in European Journal of Medicinal Chemistry in 2004.Synthetic Route of C11H13NO This article mentions the following:

A generally applicable synthesis of prenylated aromatic compounds exemplified by prenylated benzaldehydes starting from readily available acetophenones was described. The synthesized benzaldehydes were used to prepare a number of novel analogs, such as I (R = OH, R¹ = H, Cl, OMe; R = H, R¹ = H, OH; R = OMe, R¹ = OH, OMe), of Licochalcone A, a known antibacterial compound, and for the exploration of the pharmacophoric elements that are essential for the antibacterial activity. It was shown that the hydroxyl group in the A ring is essential for the activity and that the hydroxyl group in the B ring has no influence on the antibacterial effect of Licochalcone A. Furthermore, it is shown that the prenyl group at the position 5 of the B ring also has a dominating influence on the activity. This aliphatic group can be replaced by other lipophilic long chained substituents in order to maintain the activity. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Synthetic Route of C11H13NO).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Synthetic Route of C11H13NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A remarkably effective catalyst for the asymmetric transfer hydrogenation of aromatic ketones in water and air was written by Wu, Xiaofeng;Vinci, Daniele;Ikariya, Takao;Xiao, Jiangliang. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2005.Synthetic Route of C9H9NO This article mentions the following:

A Rh(III) complex generated in situ from [Cp^*RhCl₂]₂ and (1R,2R)-N-(p-toluenesulfonyl)-1,2-cyclohexanediamine (TsCYDN) serves as a remarkably effective, robust catalyst for the asym. transfer hydrogenation of aromatic ketones by HCOONa in water in air, affording alcs. in up to 99% ee. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Synthetic Route of C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Synthetic Route of C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts