Author: Jessica.F

An improved synthesis of homoproline and derivatives was written by Shuman, Robert T.;Ornstein, Paul L.;Paschal, Jonathan W.;Gesellchen, Paul D.. And the article was included in Journal of Organic Chemistry in 1990.HPLC of Formula: 36057-44-0 This article mentions the following:

Homoproline derivatives I (R = 3-Me, 4-Me, 6-Me, 4-Et, 4-OMe, 4-CMe₃) were prepared from the corresponding pyridines II in 4 steps. A key step was the treatment of N-oxides III (R = same) with Me₃SiCN and Me₂NCOCl in CH₂Cl₂ to give nitriles IV (R = same). 5,6-Benzohomoprolines V (R¹ = H, Me) were also prepared In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0HPLC of Formula: 36057-44-0).

4-methoxypicolinonitrile (cas: 36057-44-0) 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. 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. HPLC of Formula: 36057-44-0

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Equilibrium NH-acidity of substituted aminopyrimidines was written by Shkurko, O. P.;Terekhova, M. I.;Petrov, E. S.;Mamaev, V. P.;Shatenshtein, A. I.. And the article was included in Zhurnal Organicheskoi Khimii in 1981.Category: nitriles-buliding-blocks This article mentions the following:

The transmetalation method was used to determine the NH acidity (pK) of thirty-nine 2-, 4-, and 5-aminopyrimidines; the pK values ranged from 17.7 for 5-nitro-2-pyrimidinamine to 30.2 for 2-(dimethylamino)-5-pyrimidinamine. Comparison with the pK of aniline showed that the ring N atoms had an acidifying effect in the order 4-aza ≫ 2-aza > 3-aza. LFER of the pK vs. NMR chem. shifts, and inductive or resonance substituent constants were described. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Category: nitriles-buliding-blocks).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Category: nitriles-buliding-blocks

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Development of Pd/C-Catalyzed Cyanation of Aryl Halides was written by Yu, Hannah;Richey, Rachel N.;Miller, William D.;Xu, Jiansheng;May, Scott A.. And the article was included in Journal of Organic Chemistry in 2011.Computed Properties of C6H5NS This article mentions the following:

A practical method for palladium-catalyzed cyanation of aryl halides using Pd/C is described. The new method can be applied to a variety of aryl bromide and active aryl chloride substrates to effect efficient conversions. The process features many advantages over existing cyanation conditions and the practical utility of the process has been demonstrated on scale. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Computed Properties of C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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 C6H5NS

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and characterization of bis(2-cyanoethyl)aminoacetonitrile and tris(2-cyanoethyl)amine was written by Gao, Jian;Xu, Xing-you;Tang, Yan-ling;Zhang, Xing-yang. And the article was included in Huagong Kuangwu Yu Jiagong in 2003.Product Details of 7528-78-1 This article mentions the following:

Tile compounds were prepared from addition reaction of acrylonitrile with aminoacetonitrile and aqueous ammonia resp. It was characterized by IR spectra, ¹H-NMR, elemental anal., ES-MS and TG-DTA. The two compounds have similar thermal behaviors, and have high thermal stability under 300°C. 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 compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. 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.Product Details of 7528-78-1

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Nitrile – Wikipedia,
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Intramolecular photochemical proton transfer in 3-hydroxyflavone derivatives was written by Ivanova, L. L.;Demyashkevich, A. B.;Oganesyan, E. T.. And the article was included in Khimiya Vysokikh Energii in 1986.Reference of 7528-78-1 This article mentions the following:

Rate constants of the intramol. proton transfer in 3-hydroxyflavone and its 4′-methoxy- and 3′,4′-dimethoxy derivatives were studied at 77° in different solvents. The high activation barrier of the reaction was related to the characteristic geometry (non(linearity) of the intramol. H-bond. This barrier decreased with increase of the deformation polarization of the glassy medium (comprising electronic and at. polarizations). In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Reference of 7528-78-1).

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. 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.Reference of 7528-78-1

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Gewald reaction catalyzed by KF/nano-γ-Al₂O₃ under microwave irradiation was written by Hong, Zhi;Li, Xu-yao;Chen, Can-li;Chen, Guang;Wang, Han-qing;Lu, Chen-chen. And the article was included in Huaxue Shiji in 2015.HPLC of Formula: 70291-62-2 This article mentions the following:

2-Aminothiophenes were synthesized by three components Gewald reaction using KF/nano-γ-Al₂O₃ as the base catalyst with microwave irradiation method. The effects of different reaction conditions on yield were investigated. This method has advantages of using cheap and high-efficient catalyst, simple purification, short reaction time and high product yield. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2HPLC of Formula: 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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).HPLC of Formula: 70291-62-2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of some 3,5-disubstituted 1,2,4-oxadiazoles starting from aryl nitriles was written by Naveena, C. S.;Lobo, Prajwal Lourdes;Poojary, Boja;Kumari, Nalilu Sucheta. And the article was included in Organic Chemistry: An Indian Journal in 2008.Synthetic Route of C11H13NO This article mentions the following:

The synthesis of some 3,5-disubstituted 1,2,4-oxadiazoles starting from arylnitriles is described. Arylnitriles are converted to arylamidoximes and then condensed with aromatic acid chlorides to form 1,2,4-oxadiazoles. Structures of the products were characterized by anal. data and spectral studies. All compounds of the series were screened for their anti-bacterial and anti-fungal activity. Most of the tested compounds showed moderate antifungal and antibacterial activity comparable with that of the standard drug. In the experiment, the researchers used many compounds, for example, 4-iso-Butoxybenzonitrile (cas: 5203-15-6Synthetic Route of C11H13NO).

4-iso-Butoxybenzonitrile (cas: 5203-15-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Synthetic Route of C11H13NO

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Structure-guided optimization of inhibitors of acetyltransferase Eis from Mycobacterium tuberculosis was written by Punetha, Ankita;Ngo, Huy X.;Holbrook, Selina Y. L.;Green, Keith D.;Willby, Melisa J.;Bonnett, Shilah A.;Krieger, Kyle;Dennis, Emily K.;Posey, James E.;Parish, Tanya;Tsodikov, Oleg V.;Garneau-Tsodikova, Sylvie. And the article was included in ACS Chemical Biology in 2020.Category: nitriles-buliding-blocks This article mentions the following:

The enhanced intracellular survival (Eis) protein of Mycobacterium tuberculosis (Mtb) is a versatile acetyltransferase that multiacetylates aminoglycoside antibiotics abolishing their binding to the bacterial ribosome. When overexpressed as a result of promoter mutations, Eis causes drug resistance. In an attempt to overcome the Eis-mediated kanamycin resistance of Mtb, we designed and optimized structurally unique thieno[2,3-d]pyrimidine Eis inhibitors toward effective kanamycin adjuvant combination therapy. We obtained 12 crystal structures of enzyme-inhibitor complexes, which guided our rational structure-based design of 72 thieno[2,3-d]pyrimidine analogs divided into three families. We evaluated the potency of these inhibitors in vitro as well as their ability to restore the activity of kanamycin in a resistant strain of Mtb, in which Eis was upregulated. Furthermore, we evaluated the metabolic stability of 11 compounds in vitro. This study showcases how structural information can guide Eis inhibitor design. 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Novel and Direct Oxidative Cyanation Reactions of Heteroaromatic Compounds Mediated by A Hypervalent Iodine(III) Reagent was written by Dohi, Toshifumi;Morimoto, Koji;Kiyono, Yorito;Tohma, Hirofumi;Kita, Yasuyuki. And the article was included in Organic Letters in 2005.Application In Synthesis of 3-Methylthiophene-2-carbonitrile This article mentions the following:

The hypervalent iodine(III) reagent phenyliodine bis(trifluoroacetate) (PIFA) mediates the selective cyanation reactions of a wide range of electron-rich heteroaromatic compounds such as pyrroles, thiophenes, and indoles under mild conditions. These reactions proceed via a cation radical intermediate, and the key for the successful transformation presumably depends on the oxidation-reduction potential of the substrates used. The synthetic utility has been demonstrated through the conversion of these biol. important pyrroles 2f and 2g. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Application In Synthesis of 3-Methylthiophene-2-carbonitrile).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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. 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 3-Methylthiophene-2-carbonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Green halogenation of aromatic heterocycles using ammonium halide and hydrogen peroxide in acetic acid solvent was written by D’Aleo, Danielle N.;Allard, Sheena R.;Foglia, Cassandra C.;Parent, Shawna L. M.;Rohr, David J.;Gottardo, Christine;MacKinnon, Craig D.. And the article was included in Canadian Journal of Chemistry in 2013.Formula: C6H5NS This article mentions the following:

The green generation of X⁺ (X = Br, I) using hydrogen peroxide in aqueous acetic acid allows access to aromatic heterocyclic halides in yields and purities comparable to syntheses employing N-bromosuccinimide. In activated and unsubstituted thiophene rings, regioselectivity is quant. for positions to the sulfur; pyrroles also give quant. reactions, at least initially. Deactivated rings, including furans and thiazoles, as well as thiophenes with strongly electron-withdrawing groups showed little to no reactivity under the conditions investigated. The reaction shows remarkable functional group tolerance (to alc., nitro, alkyl, halo, and carbonyl groups), as shown through reaction with substituted phenols. In all bromination reactions, reaction yields and regiochem. were very similar to reactions involving N-bromosuccinimide in THF solvent. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Formula: C6H5NS).

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. 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.Formula: C6H5NS

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts