Category: nitriles-buliding-blocks

4-(Tetrazolylalkyl)piperidine-2-carboxylic acids. Potent and selective N-methyl-D-aspartic acid receptor antagonists with a short duration of action was written by Ornstein, Paul L.;Schoepp, Darryle D.;Arnold, M. Brian;Leander, J. David;Lodge, David;Paschal, Jonathan W.;Elzey, Tom. And the article was included in Journal of Medicinal Chemistry in 1991.Formula: C7H6N2O This article mentions the following:

A series of trans– and cis-4-(tetrazolylalkyl)piperidine-2-carboxylic acids I (R = H, Me) and II (n = 1, R = H, Me; n = 2-4, R = H) as potent and selective N-methyl-D-aspartic acid (NMDA) receptor antagonists were prepared and evaluated in vitro in both receptor binding assays and in a cortical-wedge preparation to determine affinity, potency, and selectivity. The new amino acids were also evaluated in vivo for their ability to block NMDA-induced convulsions in neonatal rats and NMDA-induced lethality in mice. The most potent compound of this series was I (R = H). I (R = H) blocked both NMDA-induced convulsions in neonatal rats and NMDA-induced lethality in mice. This is the first example of an NMDA receptor antagonist that incorporates a tetrazole moiety as an ω-acid bioisostere. These amino acid antagonists are also unique from their phosphonic acid counterparts in that they have a shorter duration of action in vivo. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Formula: C7H6N2O).

4-methoxypicolinonitrile (cas: 36057-44-0) 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.Formula: C7H6N2O

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Synthesis of 4-aminothieno[2,3-b]pyridine-5-carboxylic acids was written by Lalezari, Iradj. And the article was included in Journal of Heterocyclic Chemistry in 1979.Recommanded Product: 70291-62-2 This article mentions the following:

The title compounds I [R = R¹ = Me or RR¹ = (CH₂)_n, n = 3,4,5] were prepared in ∼80% yields by condensing 2-amino-3-cyanothiophenes with Et 3-aminocrotonate in the presence of p-MeC₆H₄SO₃H, EtONa-catalyzed cyclization of the resulting II, and hydrolysis. 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: 70291-62-2).

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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Recommanded Product: 70291-62-2

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One-pot synthesis of secondary amines from alcohols and nitroarenes on TiO₂ loaded with Pd nanoparticles under UV irradiation was written by Selvam, Kaliyamoorthy;Sakamoto, Hirokatsu;Shiraishi, Yasuhiro;Hirai, Takayuki. And the article was included in New Journal of Chemistry in 2015.Product Details of 10282-32-3 This article mentions the following:

Photoirradiation (λ > 300 nm) of TiO₂ loaded with Pd nanoparticles (2%, ∼5 nm diameter) in water containing benzyl alc. and nitrobenzene at room temperature successfully produces the corresponding secondary amine (N-benzylaniline) with 96% yield. This is achieved via three consecutive catalytic reactions: (i) photocatalytic oxidation of alc. (aldehyde formation) and reduction of nitrobenzene (aniline formation); (ii) catalytic condensation of the formed aldehyde with aniline on the TiO₂ surface (imine formation); and, (iii) photocatalytic hydrogenation of the formed imine (secondary amine formation). This catalytic system successfully produces several kinds of secondary amines, even those containing reducible substituents such as -CN, -COOH, or -CHO with >76% yields. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Product Details of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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).Product Details of 10282-32-3

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Contribution to our Knowledge of the Terpenes and the Ethereal Oils. 91st Paper. (C) The Behavior of β-Cyclohexylethylamine toward Nitrous Acid was written by Wallach, O.. And the article was included in Justus Liebigs Annalen der Chemie in 1908.SDS of cas: 4435-14-7 This article mentions the following:

(Cf. Ibid.). Cyclohexylacetonitrile, b. 215°, [n]_D¹⁸ 1.4575 prepared from the amide of cyclohexylacetic acid, on reduction, yielded β-cyclohexylethylamine, b. 188-9°, [n]_D¹⁹ 1.4647. With HNO₂, the latter did not form a 7-ring system, but a little cyclohexylethylene, b. 132-7°, and the alcohols C₆H₁₁.CH₂.CH₂OH and. C₆H₁₁.CH(OH).Me, which were separated by oxidation with chromic acid and formation of semicarbazones. In this way, cyclohexylacetaldehyde, semicarbazone, m. 132-4°, and cyclohexylmethylketone, semicarbazone, m. 172-3°, were obtained, while the acids formed in the oxidation were found to be cyclohexylacetic and adipic acids. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7SDS of cas: 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.SDS of cas: 4435-14-7

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Synthesis of Substituted Quinazolin-4(3H)-imines From Aryldiazonium Salts, Nitriles and 2-Cyanoanilines via A Metal-Free Tandem Approach was written by Ramanathan, Mani;Liu, Yi-Hung;Peng, Shie-Ming;Liu, Shiuh-Tzung. And the article was included in Organic Letters in 2017.Recommanded Product: 53312-77-9 This article mentions the following:

A transition metal-free synthesis of multisubstituted quinazolin-4(3H)-imines has been realized by the direct reaction of aryldiazonium salts, nitriles, and 2-cyanoanilines in a one-pot fashion. This strategy utilizes the in situ formation of reactive N-arylnitrilium intermediate, which undergoes further tandem cyclization with consecutive formation of N-C bonds. Broad functional group compatibility, mild conditions, shorter time, and operational simplicity are the notable features of this report. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Recommanded Product: 53312-77-9).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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.Recommanded Product: 53312-77-9

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A novel multiple-stage antimalarial agent that inhibits protein synthesis was written by Baragana, Beatriz;Hallyburton, Irene;Lee, Marcus C. S.;Norcross, Neil R.;Grimaldi, Raffaella;Otto, Thomas D.;Proto, William R.;Blagborough, Andrew M.;Meister, Stephan;Wirjanata, Grennady;Ruecker, Andrea;Upton, Leanna M.;Abraham, Tara S.;Almeida, Mariana J.;Pradhan, Anupam;Porzelle, Achim;Martinez, Maria Santos;Bolscher, Judith M.;Woodland, Andrew;Luksch, Torsten;Norval, Suzanne;Zuccotto, Fabio;Thomas, John;Simeons, Frederick;Stojanovski, Laste;Osuna-Cabello, Maria;Brock, Paddy M.;Churcher, Tom S.;Sala, Katarzyna A.;Zakutansky, Sara E.;Jimenez-Diaz, Maria Belen;Sanz, Laura Maria;Riley, Jennifer;Basak, Rajshekhar;Campbell, Michael;Avery, Vicky M.;Sauerwein, Robert W.;Dechering, Koen J.;Noviyanti, Rintis;Campo, Brice;Frearson, Julie A.;Angulo-Barturen, Inigo;Ferrer-Bazaga, Santiago;Gamo, Francisco Javier;Wyatt, Paul G.;Leroy, Didier;Siegl, Peter;Delves, Michael J.;Kyle, Dennis E.;Wittlin, Sergio;Marfurt, Jutta;Price, Ric N.;Sinden, Robert E.;Winzeler, Elizabeth A.;Charman, Susan A.;Bebrevska, Lidiya;Gray, David W.;Campbell, Simon;Fairlamb, Alan H.;Willis, Paul A.;Rayner, Julian C.;Fidock, David A.;Read, Kevin D.;Gilbert, Ian H.. And the article was included in Nature (London, United Kingdom) in 2015.Formula: C12H14N2O This article mentions the following:

There is an urgent need for new drugs to treat malaria, with broad therapeutic potential and novel modes of action, to widen the scope of treatment and to overcome emerging drug resistance. Here we describe the discovery of DDD107498, a compound with a potent and novel spectrum of antimalarial activity against multiple life-cycle stages of the Plasmodium parasite, with good pharmacokinetic properties and an acceptable safety profile. DDD107498 demonstrates potential to address a variety of clin. needs, including single-dose treatment, transmission blocking and chemoprotection. DDD107498 was developed from a screening program against blood-stage malaria parasites; its mol. target has been identified as translation elongation factor 2 (eEF2), which is responsible for the GTP-dependent translocation of the ribosome along mRNA, and is essential for protein synthesis. This discovery of eEF2 as a viable antimalarial drug target opens up new possibilities for drug discovery. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Formula: C12H14N2O).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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. Formula: C12H14N2O

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Exploring Homogeneous Conditions for Mild Buchwald-Hartwig Amination in Batch and Flow was written by Kashani, Saeed K.;Jessiman, Jacob E.;Newman, Stephen G.. And the article was included in Organic Process Research & Development in 2020.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

The use of high throughput experimentation to identify a number of conditions that enable Buchwald-Hartwig reactions to be carried out using readily available ligands (e.g. XantPhos) with DBU as a soluble, functional group tolerant, homogeneous base was described. Application of this system to diverse aminations in batch and flow were demonstrated, as was the translation of this technique to performing continuous Mizoroki-Heck and Sonogashira coupling reactions. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Name: 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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.Name: 4-(Benzylamino)benzonitrile

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Divergent synthesis of 2-methylthioindole and 2-unsubstituted indole derivatives mediated by SOCl₂ and dimethyl/diethyl sulfoxides was written by Zhang, Jingran;Zhang, Beibei;He, Jiaxin;Shi, Haofeng;Du, Yunfei. And the article was included in Organic & Biomolecular Chemistry in 2022.Application of 1483-54-1 This article mentions the following:

A metal-free divergent synthesis of indole compounds dependent on a reagent via intramol. C(sp²)-H amination was described. The reaction of 2-vinylanilines with DMSO/SOCl₂ at 70 ° was found to give 2-thiomethylindoles, while replacing DMSO with di-Et sulfoxide afforded 2-unsubstituted indoles in a highly selective manner. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Application of 1483-54-1).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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.Application of 1483-54-1

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Nucleophilic and Radical Heptafluoroisopropoxylation with Redox-Active Reagents was written by Tong, Chao-Lai;Xu, Xiu-Hua;Qing, Feng-Ling. And the article was included in Angewandte Chemie, International Edition in 2021.Category: nitriles-buliding-blocks This article mentions the following:

The practical and efficient heptafluoroisopropoxylation reactions through the invention of a series of redox-active N-OCF(CF₃)₂ reagents e.g., I were described. These reagents were readily prepared from the oxidative heptafluoroisopropylation of hydroxylamines e.g., II with AgCF(CF₃)₂. The substitutions on the nitrogen atom significantly affected the properties and reactivities of N-OCF(CF₃)₂ reagents. Accordingly, two types of N-OCF(CF₃)₂ reagents including I and III were used as OCF(CF₃)₂ anion and radical precursors, resp. This protocol enables the direct heptafluoroisopropoxylation of a range of substrates, delivering the corresponding products in moderate to excellent yields. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Category: nitriles-buliding-blocks).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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.Category: nitriles-buliding-blocks

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Selective Synthesis of Secondary and Tertiary Amines by Reductive N-Alkylation of Nitriles and N-Alkylation of Amines and Ammonium Formate Catalyzed by Ruthenium Complex was written by Alshakova, Iryna D.;Nikonov, Georgii I.. And the article was included in ChemCatChem in 2019.HPLC of Formula: 4714-63-0 This article mentions the following:

A ruthenium catalytic system for the syntheses of secondary and tertiary amines via reductive N-alkylation of nitriles and N-alkylation of primary amines is proposed. Isomeric ruthenium complexes catalyzed transfer hydrogenation and N-alkylation of nitriles in ethanol to give secondary amines. Unsym. secondary amines can be produced by N-alkylation of primary amines with alcs. via the borrowing hydrogen methodol. Aliphatic amines were obtained with excellent yields, while only moderate conversions were observed for anilines. Based on kinetic and mechanistic studies, it is suggested that the rate determining step is the hydrogenation of intermediate imine to amine. Finally, ammonium formate was applied as the amination reagent for alcs. in the presence of ruthenium catalyst. Secondary amines were obtained from primary alcs. within 24 h at 100 °C, and tertiary amines can be produced after prolonged heating. Secondary alcs. can only be converted to secondary amines with moderate yield. Based on mechanistic studies, the process is suggested to proceed through an ammonium alkoxy carbonate intermediate, where carbonate acts as an efficient leaving group. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0HPLC of Formula: 4714-63-0).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In 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.HPLC of Formula: 4714-63-0

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Nitrile – Wikipedia,
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