Nitriles-buliding-blocks

Synthesis and Antiprotozoal Activity of Cationic 1,4-Diphenyl-1H-1,2,3-triazoles was written by Bakunov, Stanislav A.;Bakunova, Svetlana M.;Wenzler, Tanja;Ghebru, Maedot;Werbovetz, Karl A.;Brun, Reto;Tidwell, Richard R.. And the article was included in Journal of Medicinal Chemistry in 2010.Reference of 60979-25-1 This article mentions the following:

Novel dicationic triazoles, e.g. I and II, were synthesized by the Pinner method from the corresponding dinitriles, prepared via the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The type and the placement of cationic moieties as well as the nature of aromatic substituents influenced in vitro antiprotozoal activities of dicationic triazoles against Trypanosoma brucei rhodesiense, Plasmodium falciparum, and Leishmania donovani and their cytotoxicity for mammalian cells. Eight congeners displayed antitrypanosomal IC₅₀ values below 10 nM. Thirty-nine dications were more potent against P. Falciparum than pentamidine (IC₅₀ = 58 nM), and eight analogs were more active than artemisinin (IC₅₀ = 6 nM). Diimidazoline II exhibited antiplasmodial IC₅₀ value of 0.6 nM. Seven congeners administered at 4 × 5 mg/kg by the i.p. route cured at least three out of four animals in the acute mouse model of African trypanosomiasis. At 4 × 1 mg/kg, diamidine I displayed better antitrypanosomal efficacy than melarsoprol, curing all infected mice. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Reference of 60979-25-1).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) 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. Reference of 60979-25-1

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Efficient three-component Gewald reactions under Et₃N/H₂O conditions was written by Abaee, M. Saeed;Cheraghi, Somayeh. And the article was included in Journal of Sulfur Chemistry in 2014.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

In a medium consisting of triethylamine and water, α-methylene ketones undergo room temperature Gewald reactions with elemental sulfur and Et cyanoacetate (or malononitrile) to yield 2-aminothiophene derivatives efficiently within short time periods. Because of the high polarity of the medium, products precipitate in the reaction mixtures spontaneously. This makes isolation of the products easy by simple filtration and avoids cumbersome chromatog. separations Mechanistic studies suggest that the reactions proceed via a Knoevenagel condensation pathway. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Efficient New Protocols for Converting Primary Amides into Nitriles Initiated by P(NMe₂)₃, PCl₃, or P(OPh)₃ was written by Talbi, Imen;Efrit, Mohamed Lotfi;Touil, Soufiane. And the article was included in ACS Omega in 2018.Computed Properties of C8H8N2S This article mentions the following:

Three efficient and high-yielding procedures have been developed for the conversion of primary amides into nitriles, mediated by hitherto unexplored P(NMe₂)₃, PCl₃, or P(OPh)₃. The reactions were conducted under operationally simple and mild conditions and displayed broad substrate scope and good functional group tolerance. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Computed Properties of C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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.Computed Properties of C8H8N2S

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Nitrile – Wikipedia,
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Basicity of some amines in acetonitrile was written by Peips, M.;Koppel, U.;Pihl, V.;Koppel, I.. And the article was included in Reaktsionnaya Sposobnost Organicheskikh Soedinenii in 1976.Application of 7528-78-1 This article mentions the following:

The pKBH+ values of several amines in MeCN were linearly correlated with the Taft σ* constants when a factor taking into account the primary, secondary, or tertiary nature of the amine was used. Although the pKBH+ values in MeCN and in H2O differed by 5-8 orders of magnitude, the amines exhibited comparable sensitivity to structural effects in these solvents. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Application of 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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. 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.Application of 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and x-ray crystal structure of four μ₂-phenoxy oxygen bridged macrocyclic binuclear cadmium(II) complexes with pendant arms was written by Xu, Xin-You;Meng, Qing-Guo;Luo, Qin-Hui;Shen, Meng-Chang;Hung, Xiao-Yun;Wu, Qiang-Jin. And the article was included in Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry in 1997.Application In Synthesis of 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

Four binuclear Cd(II) macrocyclic complexes were synthesized by [2+2] Schiff base condensation of tris(3-aminopropyl)amine (trpn) with sodium 2,6-diformyl-4-R-phenolate (R = CH₃, L¹; R = CH₃O, L²; R = Br, L³; R = Cl, L⁴) in the presence of Cd(ClO₄)₂·6H₂O. The crystal structure of [Cd₂L²](ClO₄)₂·0.5MeOH was determined by x-ray diffraction. The crystal is triclinic, space group P1̅, a 10.455(6), b 11.451(4), c 20.130(6) Å, Z = 2, α 105.75(3), β 82.84(3), γ 97.21(3)°, R = 0.052, R_w = 0.064. The crystal structure, spectral characterization and molar conductivity show that two Cd(II) ions are bridged by two μ₂-phenoxy O atoms. Each Cd(II) atom is located in a N₄O₂ coordination environment. The coordination geometry around the Cd(II) is a distorted octahedron. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Application In Synthesis of 3,3′,3”-Nitrilotripropanenitrile).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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 3,3′,3”-Nitrilotripropanenitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Activation of elemental sulfur by electrogenerated cyanomethyl anion: synthesis of substituted 2-aminothiophenes by the Gewald reaction was written by Feroci, Marta;Chiarotto, Isabella;Rossi, Leucio;Inesi, Achille. And the article was included in Advanced Synthesis & Catalysis in 2008.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

The activation of elemental sulfur (S₈) has been achieved using the electrogenerated cyanomethyl anion [easily obtained by galvanostatic reduction from acetonitrile/tetraethylammonium hexafluorophosphate (MeCN-Et₄NPF₆)]. The “activated” sulfur reacted with ylidenemalononitriles to give substituted 2-aminothiophenes in very high yields. This variation of the Gewald reaction has been carried out using only catalytic amounts of electricity and supporting electrolyte. A proposed mechanism for the interaction between S₈ and cyanomethyl anion is described. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and antiallergy activity of [1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one derivatives. II. 6-Alkyl- and 6-cycloalkylalkyl derivatives was written by Yokohama, Shuichi;Miwa, Tamotsu;Aibara, Shunzo;Fujiwara, Hiroyuki;Matsumoto, Hiroo;Nakayama, Kiyoshi;Iwamoto, Teiji;Mori, Mikio;Moroi, Reimei. And the article was included in Chemical & Pharmaceutical Bulletin in 1992.Application In Synthesis of 2-Cyclohexylacetonitrile This article mentions the following:

A series of 6-alkyl- or 6-(cycloalkylalkyl)-[1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-ones, including I (R = cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylpropyl, cycloheptylethyl, cyclooctylethyl, cyclododecylethyl), was synthesized from the corresponding 1,3,4-thiadiazol-5-amines II and the antiallergic activities of the products were evaluated. Among these compounds 6-(2-cyclohexylethyl)-[1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one (I, R = cyclohexylethyl), whose x-ray crystallog. stereostructure was determined, is a promising new antiallergic agent, which has low toxicity and dual activity as a leukotriene D₄ receptor antagonist and as an orally active mast cell stabilizer. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Application In Synthesis of 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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.Application In Synthesis of 2-Cyclohexylacetonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Function-Structure Relationship in Metal-Organic Frameworks for Mild, Green, and Fast Catalytic C-C Bond Formation was written by Razavi, Sayed Ali Akbar;Morsali, Ali. And the article was included in Inorganic Chemistry in 2019.Formula: C18H10N2 This article mentions the following:

Tunability in chem. functionality is a promising characteristic of metal-organic frameworks (MOFs), which plays an important role in developing and improving the practical applications of MOFs. Here, authors applied this important feature of MOFs to be in line with sustainable development and green chem. principles through the synthesis of MOF-based heterogeneous organocatalysts. According to their green functionalization strategy, some isostructural MOFs (azine decorated TMU-4 with the formula [Zn(OBA)(BPDB)_0.5]_n·2DMF, azine-Me functionalized TMU-5 with the formula [Zn(OBA)(BPDH)_0.5]_n·1.5DMF, dihydro-tetrazine decorated TMU-34 with the formula [Zn(OBA)(H₂DPT)_0.5]_n·DMF, and tetrazine functionalized TMU-34(-2H) with the formula [Zn(OBA)(DPT)_0.5]_n·DMF, where H₂OBA = 4,4′-oxybis(benzoic acid), BPDB = 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene, BPDH = 2,5-bis(4-pyridyl)-3,4-diaza-2,4-hexadiene, H₂DPT = 3,6-di(pyridin-4-yl)-1,4-dihydro-1,2,4,5-tetrazine, and DPT = 3,6-di(pyridin-4-yl)-1,2,4,5-tetrazine) have been applied for mild, green, and fast Knoevenagel condensation. These frameworks display different Lewis basic catalytic activities owing to their different functionality and function accessibility. Contrary to extensive articles published about Knoevenagel condensation, this study involves the rare examples in Knoevenagel condensation with such mild conditions (room temperature and atm. pressure) and with a green solution (water as the solvent). Due to the combined synergic effects of the Lewis basicity of TMU-frameworks, the amphoteric and hydrogen bond-participating nature of water mols., maximum conversion times are reached just after 30 min (for TMU-5) and 60 min (for TMU-34). Stability and recyclability tests show that TMU-5 and TMU-34 are completely stable in water at reaction conditions and can retain their crystallinity, porosity, and functionality even after five cycles without any specific reduction in their catalytic conversion. Since, in many cases, amine decorated MOFs are applied in Knoevenagel catalyzed condensation, this study is beneficial in providing information about the effects of azine and tetrazine functional groups in reactant activation and the acceleration of Knoevenagel condensation. In this work, according to green chem. principles and sustainable development, we applied some azine and tetrazine TMU-frameworks as basic heterogeneous organocatalysts for mild, green, and fast Knoevenagel condensation in water at room temperature and atm. pressure. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Formula: C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Formula: C18H10N2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A facile microwave assisted synthesis and anti-inflammatory activity of thiophene[3,2- e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one derivatives was written by Kaur, Rajwinder;Rao, Akkinepally Raghuram;Chadha, Renu;Thakur, Nishant;Goswami, Manish. And the article was included in International Journal of Pharmaceutical Sciences Review and Research in 2016.Category: nitriles-buliding-blocks This article mentions the following:

A series of novel substituted triazolo thieno pyrimidines (5-12) was synthesized by employing innovative synthetic methods. Two methods (A and B) were employed for the synthesis of compounds 3-12. Method B (microwave assisted) was found to be facile, economic and less time consuming compared to conventional method (method A) adopted. The microwave irradiation provided an environment-friendly, remarkable rate of acceleration for the reaction with reduced reaction time and in some cases (under MW irradiation) the yields are also substantially higher. Anti-inflammatory activity and mast cell degranulation studies of synthesized compounds were carried out. Indomethacin was taken as a reference standard in carrageenan induced rat paw edema model for anti-inflammatory studies and in mast cell degranulation studies disodium cromoglycate was used for comparison. All compounds showed a good anti-inflammatory response and mast cell stabilization. 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 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.Category: nitriles-buliding-blocks

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Nitrile – Wikipedia,
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Synthesis of tetraethyl ester of 5-aminothiophene by phase transfer catalysis was written by Hu, Kai;Ding, Xiang-Yu;Jia, Xiang-Man;Jiang, Ye;Liu, Feng-Hua. And the article was included in Zhongguo Xiandai Yingyong Yaoxue in 2008.Reference of 58168-20-0 This article mentions the following:

A method for the synthesis of the title compound [i.e., tetra-Et ranelate; 5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-2-(ethoxycarbonyl)-3-thiopheneacetic acid] is reported here. The synthesis of this tetra-Et ester of 5-aminothiophene was achieved by a by phase transfer catalyzed reaction and the best reaction conditions were determined Cyclization of 3-oxopentanedioic acid 1,5-di-Et ester with propanedinitrile and sulfur provided 5-amino-4-cyano-2-(ethoxycarbonyl)-3-thiopheneacetic acid Et ester. Then in acetone, tetra-Et ester of 5-aminothiophene was synthesized from 5-aminothiophene by phase transfer catalysis with Et bromoacetate in presence of a crown ether using potassium carbonate as solid base. Under optimized reaction conditions, crown ether was used as phase transfer catalyst, the molar ratio of alkylating reagent, alkali and reagent was 2.2 and 2.5 resp., the reaction temperature was 60° and the reaction time was 6 h. This method provides high product yield and purity. This is a key intermediate for strontium ranelate (a bone formation stimulant). In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Reference of 58168-20-0).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) 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.Reference of 58168-20-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts