Nitriles-buliding-blocks

Aluminum-Catalyzed Asymmetric Alkylations of Pyridyl-Substituted Alkynyl Ketones with Dialkylzinc Reagents was written by Friel, Donna K.;Snapper, Marc L.;Hoveyda, Amir H.. And the article was included in Journal of the American Chemical Society in 2008.Recommanded Product: 36057-44-0 This article mentions the following:

Alkylations of pyridyl-substituted ynones with Et₂Zn and Me₂Zn, promoted by amino acid-based chiral ligands in the presence of Al-based alkoxides, afford tertiary propargyl alcs. efficiently in 57% to >98% ee. Two easily accessible chiral ligands are identified as optimal for reactions of the two dialkylzinc reagents. Catalytic alkylations with Et₂Zn require a chiral ligand carrying two amino acid moieties (valine and phenylalanine) along with a p-trifluoromethylphenylamide C-terminus. In contrast, reactions with Me₂Zn are most effectively promoted in the presence of a chiral ligand containing a single amino acid (benzyl cysteine), capped by an n-butylamide. Enantiomerically enriched tertiary alcs. bearing a pyridyl and an alkyne substituent can be functionalized in a variety of manners to furnish a wide range of difficult-to-access acyclic and heterocyclic structures; two noteworthy examples are Cu-catalyzed protocols for conversion of tertiary propargyl alcs. to enantiomerically enriched tetrasubstituted allenes and bicyclic amides that bear an N-substituted quaternary carbon stereogenic center. Mechanistic models that account for the trends and enantioselectivity levels are provided. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Recommanded Product: 36057-44-0).

4-methoxypicolinonitrile (cas: 36057-44-0) 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).Recommanded Product: 36057-44-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Amination of acrylonitrile in liquid ammonia was written by Murohashi, Susumu. And the article was included in Nagaoka Kogyo Tanki Daigaku Koto Semmon Gakko Kenkyu Kiyo in 1968.Name: 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

The title reaction was studied with or without a catalyst. Acrylonitrile (1 mole) was treated with liquid NH3 (>10 moles) in an autoclave at 100° for 30 min. in the presence of Raney Cu or Co to give mono(β-cyanoethyl)amine as the main product in 80% yield. Tris(β-cyanoethyl)amine was obtained when no catalyst or the Raney catalyst together with a polymerization inhibitor was used, while the bis- and tris(β-cyanoethyl)amines were produced in the presence of Raney Ni. After the amination, only the Co catalyst among Raney metal catalysts kept the ability as a hydrogenation catalyst. Successive amination and hydrogenation of acrylonitrile without isolation of the intermediate or further addition of the catalyst gave 1,3-propanediol in 80% yield. Gas chromatographic determination and life of the catalyst were also discussed. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Name: 3,3′,3”-Nitrilotripropanenitrile).

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. 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.Name: 3,3′,3”-Nitrilotripropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of 2-azo-3-cyano-5-carbethoxy thiophene derivatives and their application on polyester fibers was written by Sabnis, Ram W.;Rangnekar, Dinesh W.. And the article was included in Journal of Chemical Technology and Biotechnology in 1990.Application In Synthesis of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate This article mentions the following:

Synthesis of 2-(hetaryl or aryl)-azo thiophene derivatives was achieved by diazotization of Et 2-amino-3-cyano-5-carbethoxythiophene-4-acetate (I) using nitrosylsulfuric acid and coupling with suitable heterocyclic hydroxy and N,N-dialkyl-substituted aryl amines. I was synthesized in one pot and in excellent yield from di-Et acetonedicarboxylate, S and malonitrile, using HNEt₂ as a catalyst, following the Gewald synthesis. The spectral properties of these dyes were studied. The dyes when applied as disperse dyes on polyester fibers gave excellent results. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Application In Synthesis of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Identification, Design and Biological Evaluation of Heterocyclic Quinolones Targeting Plasmodium falciparum Type II NADH:Quinone Oxidoreductase (PfNDH2) was written by Leung, Suet C.;Gibbons, Peter;Amewu, Richard;Nixon, Gemma L.;Pidathala, Chandrakala;Hong, W. David;Pacorel, Benedicte;Berry, Neil G.;Sharma, Raman;Stocks, Paul A.;Srivastava, Abhishek;Shone, Alison E.;Charoensutthivarakul, Sitthivut;Taylor, Lee;Berger, Olivier;Mbekeani, Alison;Hill, Alasdair;Fisher, Nicholas E.;Warman, Ashley J.;Biagini, Giancarlo A.;Ward, Stephen A.;O’Neill, Paul M.. And the article was included in Journal of Medicinal Chemistry in 2012.Application In Synthesis of 4-(Morpholinomethyl)benzonitrile This article mentions the following:

Following a program undertaken to identify hit compounds against NADH:ubiquinone oxidoreductase (PfNDH2), a novel enzyme target within the malaria parasite Plasmodium falciparum, hit to lead optimization led to identification of CK-2-68, a mol. suitable for further development. To reduce ClogP and improve solubility of CK-2-68 incorporation of a variety of heterocycles, within the side chain of the quinolone core, was carried out, and this approach led to a lead compound SL-2-25 (I). I has IC₅₀s in the nanomolar range vs. both the enzyme and whole cell P. falciparum (IC₅₀ = 15 nM PfNDH2; IC₅₀ = 54 nM (3D7 strain of P. falciparum)) with notable oral activity of ED₅₀/ED₉₀ of 1.87/4.72 mg/kg vs. Plasmodium berghei (NS Strain) in a murine model of malaria when formulated as a phosphate salt. Analogs in this series also demonstrate nanomolar activity against the bc₁ complex of P. falciparum providing the potential added benefit of a dual mechanism of action. The potent oral activity of 2-pyridyl quinolones underlines the potential of this template for further lead optimization studies. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Application In Synthesis of 4-(Morpholinomethyl)benzonitrile).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) 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.Application In Synthesis of 4-(Morpholinomethyl)benzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Organic catalysts. XL. Synthetic dehydrogenases. 8 was written by Mix, Hermann;Krause, Hans Walter. And the article was included in Chemische Berichte in 1956.Synthetic Route of C8H8N2 This article mentions the following:

Some isatins, CMe:CH.CH:CR.C:C.NH.CO.CO (I), and N-(7-methylisatin-4-carbonyl)amino acid Et esters (II), substituted in the 4-position, are prepared and tested for their dehydrogenase activity. Treating p-MeC₆H₄CO₂H with fuming HNO₃ yields 4,3-Me(O₂N)C₆H₃CO₂H, m. 188-9°, which, reduced with Raney Ni in dioxane at 120° and 100 atm., gives 90% 4,3-Me(H₂N)C₆H₃CO₂H (III), m. 162°. Heating 5 g. III in 150 cc. H₂O containing 2 cc. concentrated H₂SO₄ with 5.5 g. CCl₃CHO.H₂O (IV) and 6.5 g. (HONH₂)₂.H₂SO₄ (V) yields 3-isonitrosoacetamido-4-methylbenzoic acid which (10 g.), heated in 22 cc. concentrated H₂SO₄ at 85-90° and kept 0.5 hr. at 95-100°, gives 72% I (R = CO₂H) (VI), yellow-red needles, m. 278-80°; Et ester, prepared by heating 5 g. VI in 150 cc. EtOH-HCl 0.5 hr. on a water bath and chromatographing over Al₂O₃, orange rods, m. 205°. Heating 5 g. 4,3-Me(H₂N)C₆H₃CN, m. 81°, 6.3 g. IV, and 7.5 g. V in 430 cc. H₂O and 3 cc. concentrated H₂SO₄ gives 2-2.5 g. isonitroso compound which, heated with concentrated H₂SO₄, yields I (R = CONH₂), brick-red crystals, decompose above 270°. Adding 0.94 cc. ClCO₂Et dropwise to a solution of 2 g. VI and 2.28 g. Bu₃N in 20 cc. CHCl₃ at -5°, stirring the mixture 0.5 hr. at -5°, then adding 900 mg. PhNH₂, and stirring the mixture 12 hrs. give I (R = CONHPh), small red rods, m. 308°; I (R = CONEt₂), light red leaflets, m. 192°. The following II are prepared (amino acid given): alanine, light red rods, m. 254°; norvaline, light red leaflets, m. 220°; α-aminobutyric acid, red leaflets, m. 218-19°; glutamic di-Et ester, red needles, m. 171-2°; glutamic mono-Et ester, long red needles, m. 186-7°; phenylalanine, red needles, m. 225-6°; tryptophan Me ester, purple crystals, m. 254°. Treating 1.2 g. 2,4-Me₂C₆H₃NH₂ in 30 cc. H₂O and 1.16 g. concentrated H₂SO₄ with 1.7 g. IV and 1.9 g. V yields isonitrosoacetamido-p-xylene which, added to 10 cc. concentrated H₂SO₄ at 65-7° and the mixture heated 20 min. at 65-70°, gives 4,7-dimethylisatin, yellow-red precipitate, m. 261°. Reduction of 4,3-Me(O₂N)C₆H₃NHAc with Raney Ni at 120° and 100 atm. gives 100% 3,4-Me(H₂N)C₆H₃NHAc, m. 159°, which (6 g.), stirred 4-5 hrs. at 36-40° with 6 g. IV and 7.2 g. V, yields 3-isonitrosoacetamido-4-methylacetanilide. Heating the latter 45 min. in 10 cc. concentrated H₂SO₄ at 95-100° gives 4-amino-7-methylisatin, light red needles, charring above 310°. The dehydrogenase activity of these compounds has been tested by measuring the time required to decolorize a solution of 2 × 10^-5 moles methylene blue and 2.25 × 10^-4 moles DL-alanine in 71% HCONMe₂ at 40°. The results, given in a table, show that V is the most active catalyst. The introduction of the Me group at the 7-position has no effect on the dehydrogenation velocity. For the calculation of the partial velocities of the catalysis the P_S curves of some of the compounds are given. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Synthetic Route of C8H8N2).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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.Synthetic Route of C8H8N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of novel fused thienodiazaphosphorine derivatives from 2-amino-3-cyanothiophenes and Lawesson’s reagent was written by Khalladi, Khaoula;Touil, Soufiane. And the article was included in Journal of Sulfur Chemistry in 2012.Formula: C8H8N2S This article mentions the following:

In a simple one-pot procedure, treatment of 2-amino-3-cyanothiophenes with Lawesson’s reagent led to the new thieno[2,3-d][1,3,2]diazaphosphorine-6-thione-2-sulfides in good to excellent yields. A possible reaction mechanism, involving a Dimroth-type rearrangement, was proposed. The structure of obtained products was confirmed by NMR (¹H, ³¹P, and ¹³C) and IR spectroscopies and by mass spectrometry. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Formula: 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Formula: C8H8N2S

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Action of stilbene on tetrachloro-ο-benzoquinone was written by Schonberg, Alexander;Latif, Nazih. And the article was included in Journal of the American Chemical Society in 1950.COA of Formula: C8H13N This article mentions the following:

Tetrachloro-ο-quinone (I) (1 g.) and (PhCH:)₂ (II) in 30 cc. C₆H₆, exposed 13 days to sunlight, give 2,3-diphenyl-5,6,7,8-tetrachloro-1,4-benzodioxan (III), m. about 172°; III results in 70% yield on boiling 1.2 g. I and 0.9 g. II in C₆H₆ 15 hrs. in the dark. I (0.6 g.) and 0.5 g. (p-MeC₆H₄CH:)₂, exposed 10 days to sunlight, give 2-phenyl-3-(p-tolyl)-5,6,7,8-tetrachloro-1,4-benzodioxan, m. 132°. III, heated 15 min. in a C₆H₄(CO₂Et)₂ bath (oil-pump vacuum), gives II. III does not react with ο-C₆H₄(NH₂)₂ (refluxed 2 hrs. in 90% AcOH). In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7COA of Formula: C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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.COA of Formula: C8H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cp*Co(III) and Cu(OAc)₂ bimetallic catalysis for Buchwald-type C-N cross coupling of aryl chlorides and amines under base, inert gas & solvent-free conditions was written by Srivastava, Avinash K.;Sharma, Charu;Joshi, Raj K.. And the article was included in Green Chemistry in 2020.Formula: C14H12N2 This article mentions the following:

A strategy involving bimetallic catalysis with a combination of Cp*Co(CO)I₂ and Cu(OAc)₂ was used for performing Buchwald-type C-N coupling reactions of aryl chlorides RCl (R = Ph, pyridin-2-yl, 4-cyanophenyl, etc.) with amines R¹NHR² (R¹ = H, Et; R² = Pr, benzyl, 4-methoxyphenyl, etc.; R¹R² = -(CH₂)₄– and -(CH₂)₅-). The reactions proceeded at 100°C to produce excellent yields of many of the desired C-N coupled products R¹N(R)R², in 4 h, under aerobic reaction conditions. The reactions were shown to run under base-free and solvent-free conditions, enabling this strategy to work efficiently for electron-withdrawing and base-sensitive functionalities. The presented methodol. was found to be equally efficient for electron-donating functionalities as well as for primary (1°) and secondary (2°) aromatic and aliphatic amines. Moreover, the products were easily separated through the extractions of the organic aqueous layer, with this process chromatog. separations are not required. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Formula: C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Formula: C14H12N2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Charge localization in the retro-Diels-Alder fragmentation of tetralins was written by Lightner, David A.;Steinberg, Frank S.. And the article was included in Organic Mass Spectrometry in 1970.SDS of cas: 29809-13-0 This article mentions the following:

The electron-impact induced retro-Diels-Alder reaction of 5- and 6-substituted tetralins has been examined Most electron-donating groups at C-5 retard the fragmentation relative to tetralin; whereas, electron-withdrawing groups slightly increase the fragmentation. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0SDS of cas: 29809-13-0).

5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0) 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. 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.SDS of cas: 29809-13-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis, Characterization, Antimicrobial Activity Screening, and Molecular Docking Study of Pyrimidine Carbonitrile Derivatives was written by Bhat, Radhika;Begum, Noor Shahina. And the article was included in Russian Journal of Organic Chemistry in 2021.Computed Properties of C5H3ClN4 This article mentions the following:

The synthesis of pyrimidine carbonitrile derivatives I [R = 1-piperidyl, 2-phenylethylamino, 2-(1H-indol-3-ylmethylene)hydrazino, etc.] was described. The compounds I were characterized by FT-IR and ¹H and ¹³C- NMR spectroscopy and mass spectrometry. All the compounds I were evaluated for in-vitro antimicrobial activity against different bacterial and fungal strains. The min. inhibitory concentrations (MICs) of all the compounds I were validated. Compounds I [R = 2-[(3,4-dimethoxyphenyl)methylene]hydrazino, 1-piperidyl], which had the lowest MIC values were selected for cell leakage anal. and bacterial growth curve study. It was found that both the compounds I [R = 2-[(3,4-dimethoxyphenyl)methylene]hydrazino, 1-piperidyl] have potential to induce bacterial cell membrane rupture and disintegration. Field emission scanning electron microscopic anal. confirmed the effect of the selected compounds on the morphol. of both Gram-pos. (S. aureus) and Gram-neg. (E. coli) bacteria. The mechanism of interaction between the drug and the target protein of S. aureus and E. coli was studied by mol. docking. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Computed Properties of C5H3ClN4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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.Computed Properties of C5H3ClN4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts