Tag: 100-200

A new approach to the synthesis of lamotrigine and other 3,5-diamino-1,2,4-triazine derivatives was written by Ulomskii, E. N.;Shestakova, T. S.;Deev, S. L.;Rusinov, V. L.;Chupakhin, O. N.. And the article was included in Russian Chemical Bulletin in 2005.HPLC of Formula: 3218-45-9 This article mentions the following:

A new in principle method for the synthesis of 6-aryl(hetaryl)-3,5-diamino-1,2,4-triazines by decomposition of pre-synthesized tetrazolo[1,5-b][1,2,4]triazines was developed. The advantages of this method over traditional methods were demonstrated using the synthesis of a modern antiepileptic preparation lamotrigine, as an example. The crystal structure of 6-phenyltetrazolo[1,5-b][1,2,4]triazin-7-amine is presented [monoclinic, space group P2₁/c, a 10.935(2), b 6.7330(10), c 13.279(3) Å, β 93.20(3)°, V 976.1(3) ų, Z 4]. In the experiment, the researchers used many compounds, for example, 2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9HPLC of Formula: 3218-45-9).

2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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: 3218-45-9

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Nitrile – Wikipedia,
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Structure-activity relationships for inhibitors of Pseudomonas aeruginosa exoenzyme S ADP-ribosyltransferase activity was written by Saleeb, Michael;Sundin, Charlotta;Aglar, Oeznur;Pinto, Ana Filipa;Ebrahimi, Mahsa;Forsberg, Aake;Schuler, Herwig;Elofsson, Mikael. And the article was included in European Journal of Medicinal Chemistry in 2018.Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

During infection, the Gram-neg. opportunistic pathogen Pseudomonas aeruginosa employs its type III secretion system to translocate the toxin exoenzyme S (ExoS) into the eukaryotic host cell cytoplasm. ExoS is an essential in vivo virulence factor that enables P. aeruginosa to avoid phagocytosis and eventually kill the host cell. ExoS elicits its pathogenicity mainly via ADP-ribosyltransferase (ADPRT) activity. The authors recently identified a new class of ExoS ADPRT inhibitors with in vitro IC₅₀ of around 20 μM in an enzymic assay using a recombinant ExoS ADPRT domain. Herein, the authors report structure-activity relationships of this compound class by comparing a total of 51 compounds based on a thieno [2,3-d]pyrimidin-4(3H)-one and 4-oxo-3,4-dihydroquinazoline scaffolds. Improved inhibitors with in vitro IC₅₀ values of 6 μM were identified. Importantly, the authors demonstrated that the most potent inhibitors block ADPRT activity of native full-length ExoS secreted by viable P. aeruginosa with an IC₅₀ value of 1.3 μM in an enzymic assay. This compound class holds promise as starting point for development of novel antibacterial agents. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Quality Control 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. 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.Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

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Nitrile – Wikipedia,
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Synthesis of optically active 1-fluoroalkylbenzenes was written by Fritz-Langhals, Elke. And the article was included in Tetrahedron Letters in 1994.Reference of 101219-69-6 This article mentions the following:

Optically active 1-hydroxyalkyl benzenes having electron-withdrawing substituents are converted into the methanesulfonates and subsequently converted into the optically active 1-fluoroalkyl benzenes I (R = 4-cyano, 4-NO₂, 4-EtO₂C, 2-F, 4-Br, 4-O₂NC₆H₄) by use of the fluorinating agent CsF/HCONHMe. The starting alc. is also recovered, with a ratio of I:alc. depending on the solvent. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Reference of 101219-69-6).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Reference of 101219-69-6

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Antituberculous compounds. XXII. Monoalkylaminobenzothioamides was written by Kakimoto, Shichiro;Tone, Ikuko. And the article was included in Journal of Medicinal Chemistry in 1965.Safety of 4-(Ethylamino)benzonitrile This article mentions the following:

Several monoalkyl, phenyl, and benzyl derivatives of 4-aminobenzothioamide, and their precursor nitriles were prepared to test the hypothesis that the extinction coefficient, Ε_maximum of the C-N stretching vibration in the ir adsorption spectrum of the parent nitrile parallels the inhibitory action against Mycobacterium tuberculosis strain H37Rv in vitro. No conclusions were drawn. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Safety of 4-(Ethylamino)benzonitrile).

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.Safety of 4-(Ethylamino)benzonitrile

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First Gewald reaction ignited by sodium polysulfide: greener ultrasound-promoted synthesis of substituted 2-aminothiophenes in the absence of catalyst was written by Liang, Chengyuan;Lei, Dong;Wang, Xiuzhen;Zhang, Qingqing;Yao, Qizheng. And the article was included in Journal of Sulfur Chemistry in 2013.Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

In this paper, a modified and facile Gewald reaction triggered by sodium polysulfide in the absence of catalytic base was developed. This approach involves a one-pot ultrasound-irritated aqueous reaction between ketones or aldehydes, malononitrile and sodium sulfide [Na₂(S_x)] [sodium polysulfide, sodium sulfide [Na₂(S₄)], sodium sulfide [Na₂(S₆)], sodium sulfide (NaS)]. which are converted into the corresponding 2-aminothiophene derivatives in moderate to high yields. In comparison with conventional methods, the prominent features of this ultrasound-mediated procedure are exptl. simplicity, good functional group tolerance, atom efficiency, and the use of water as a green solvent. The title compounds thus formed included and amine nitrile [2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile] (I) and an analog, 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (II), 2-amino-4-ethyl-3-thiophenecarbonitrile, 2-amino-4-(phenylmethyl)-3-thiophenecarbonitrile. The synthesis of the target compounds was achieved using cyclohexanone, cyclopentanone, butanal, propanal, hexanal, benzeneacetaldehyde, benzenepropanal as starting materials. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Name: 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. 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).Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

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Nitrile – Wikipedia,
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Silica-sulfuric acid: novel, simple, efficient and reusable catalyst for hydration of nitrile to amide was written by Chandrashekharappa, Sandeep;Venugopala, Katharigatta N.;Venugopala, Rashmi;Odhav, Bharti. And the article was included in Asian Journal of Chemistry in 2016.Reference of 60979-25-1 This article mentions the following:

Silica-sulfuric acid efficiently catalyzes conversion of aliphatic, substituted aromatic and hetero aromatic nitriles to their corresponding amides in good to excellent yields under reflux condition. Products obtained were purified by column chromatog. method and characterized by ¹H NMR, ¹³C NMR and mass spectral anal. 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. 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.Reference of 60979-25-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The comparison of molecular surfaces by neural networks and its applications to quantitative structure activity studies was written by Polanski, Jaroslaw;Gasteiger, Johann;Wagener, Markus;Sadowski, Jens. And the article was included in Quantitative Structure-Activity Relationships in 1998.Application In Synthesis of 3-Amino-4-methoxybenzonitrile This article mentions the following:

Self-organizing Kohonen neural networks are used to obtain quant. structure-activity relationships. Simple mols. were selected to discuss the essential features of the transformation. Descriptors calculated from maps obtained from comparative studies with template mols. applied to the anal. of compounds derived from butane, as well as Et carboxylates and nitroanilines and aminobenzonitriles (sweet-tasting compounds) can be correlated with various mol. effects. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Application In Synthesis of 3-Amino-4-methoxybenzonitrile).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) 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. 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.Application In Synthesis of 3-Amino-4-methoxybenzonitrile

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Nitrile – Wikipedia,
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Polystyrene-Supported Palladium (Pd@PS)-Catalyzed Carbonylative Annulation of Aryl Iodides Using Oxalic Acid as a Sustainable CO Source for the Synthesis of 2-Aryl Quinazolinones was written by Ram, Shankar;Shaifali;Chauhan, Arvind Singh;Sheetal;Sharma, Ajay Kumar;Das, Pralay. And the article was included in Chemistry – A European Journal in 2019.Reference of 1483-54-1 This article mentions the following:

An efficient and convenient strategy for the synthesis of diversely substituted quinazolinones from o-carbamoyl/cyano aniline and aryl iodides using oxalic acid as a CO source under polystyrene supported palladium (Pd@PS) nanoparticles (NPs) catalyzed conditions was developed. The oxalic acid were employed as safe, economic, environmentally benign, sustainable and bench-stable, solid CO surrogate under Double-Layer-Vial (DLV) system for the synthesis of 2-aryl quinazolinones. This methodol. does not require any special high-pressure equipment like autoclaves, microwaves, etc. Moreover, a simple procedure for catalyst preparation, catalyst recyclability, easy handling of reaction, additive and base-free generation of CO, excellent to good yields and vast substrate scope were the addnl. features of developed protocol. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Reference of 1483-54-1).

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

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts