Tag: 100-200

Reactions of N-aminopyridinium derivatives. XII. Nucleophilic reactions of N-aminopyridinium derivatives was written by Ohsawa, Akio;Hirobe, Masaaki;Okamoto, Toshihiko. And the article was included in Yakugaku Zasshi in 1972.Synthetic Route of C7H6N2O This article mentions the following:

Derivatives of N-aminopyridine were synthesized and these derivatives underwent reaction with nucleophilic reagents. Progress of this reaction depended on the activity of the reagents as a nucleophilic species, substituent effect of the substrate, and reaction conditions. Electron-withdrawing nature of the substituent on the amino group determines the activity of the substrate while that of the substituent on ring C determines the orientation of the reaction, the greater the electron-withdrawing nature of ring C the greater the orientation towards the 2-position. The reaction results in addition and (or) substitution reaction and the reaction can be explained without inconsistency by assuming the progress of this reaction in 2 steps of addition and liberation even when only a substitution product is obtained. Depending on whether the addition step is reversible or irreversible, each step will be controlled either by thermokinetics or by chem. kinetics, and orientation towards the 4- or 2-position will be determined by which of these forces would be stronger. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Synthetic Route of C7H6N2O).

4-methoxypicolinonitrile (cas: 36057-44-0) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Synthetic Route of C7H6N2O

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Flexible covalent tripods in nonadentate podands: synthesis of tris[3-(6-diethylcarbamoylpyridine-2-carboxamido)propyl]amine and its complexing properties with trivalent lanthanides was written by Renaud, Fabien;Decurnex, Carole;Piguet, Claude;Hopfgartner, Gerard. And the article was included in Journal of the Chemical Society, Dalton Transactions in 2001.Electric Literature of C9H12N4 This article mentions the following:

The nonadentate podand tris[3-(6-diethylcarbamoylpyridine-2-carboxamido)propyl]amine (L¹⁴) is prepared according to a multistep strategy using the flexible tris(3-(N-methylamino)propyl)amine (Me-TRPN) covalent tripod. L¹⁴ exists as a statistical mixture of four conformers in solution whose distribution is slightly affected by protonation of the apical nitrogen atom in [L¹⁴ + H]⁺. Reactions of L¹⁴ and [L¹⁴ + H]⁺ with Ln³⁺ (Ln = La-Lu) produce flexible and poorly stable 1:1 podates [Ln(L¹⁴)]³⁺ and [Ln(L¹⁴ + H)]⁴⁺ in which the terdentate chelating binding units exhibit partial dynamic on-off complexation equilibrium In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Electric Literature of C9H12N4).

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. 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.Electric Literature of C9H12N4

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A simplified method to prepare 2-amino-5-bromopyrimidine. A laboratory experiment was written by Fichter, Richard;Bonvicino, Guido E.. And the article was included in Journal of Chemical Education in 1985.Quality Control of 2-Aminopyrimidine-5-carbonitrile This article mentions the following:

An experiment for undergraduate organic chem. students is described in the preparation of 2-amino-5-bromopyridine by the bromination of 2-aminopyrimidine. The preparation of 2-amino-5-cyanopyrimidine from 2-amino-5-bromopyrimidine is also described. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Quality Control of 2-Aminopyrimidine-5-carbonitrile).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) 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. 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.Quality Control of 2-Aminopyrimidine-5-carbonitrile

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Synthesis of Silicon-Stereogenic Silanols Involving Iridium-Catalyzed Enantioselective C-H Silylation Leading to a New Ligand Scaffold was written by Zhang, Hongpeng;Zhao, Dongbing. And the article was included in ACS Catalysis in 2021.HPLC of Formula: 36057-44-0 This article mentions the following:

Despite a growing focus on the construction of highly enantioenriched silicon-stereogenic organosilicon compounds, the enantioselective synthesis of silicon-stereogenic silanols through asym. catalysis remains a considerable challenge. Herein, we realized enantioselective construction of silicon-stereogenic diarylsilanols via an Ir-catalyzed C-H silylation of diarylsilanols along with stereospecific substitution or Tamao-Fleming oxidation This strategy gives rise to a class of chiral diol catalyst cores (PSiOLs). Transformation of PSiOLs led to the ligand possessing both Si and P-stereocenters, which is capable of inducing excellent enantioselectivity in the rhodium(I)-catalyzed conjugate 1,4-addition of aryl boronic acids to cyclohexenone. 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 compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. 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.HPLC of Formula: 36057-44-0

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Studies on monolayers. 1. Surface tension and absorption spectroscopic measurements of monolayers of surface-active azo and stilbene dyes was written by Heesemann, Juergen. And the article was included in Journal of the American Chemical Society in 1980.Formula: C8H6N2O2 This article mentions the following:

In order to develop new mols. as functional components of monolayer assemblies a series of 9 surface-active azo and stilbene compounds were synthesized. Their monolayer properties at the air-water interface were studied by surface pressure-surface area measurements and spectroscopic techniques. Small changes in the mol. structure of the surfactants (such as length of the fatty acid chain, type of the chromophore, etc.) have an immense influence on the monolayer properties. For monolayers of some of the dyes, van der Waals-like isotherms are obtained, which show a liquid expanded state, a phase transition region, and a condensed state. Monolayer absorbance spectra show that in the liquid expanded state at 100-110 Ų/mol. the chromophores lie flatly on the water surface, forming monomers. Surface absorbance-surface area isotherms show that the phase transition region of the isotherms can be assigned to a change of orientation of the chromophore axis (horizontal → vertical) and an aggregation of the chromophores (monomers → H aggregates). High dichroic and narrow absorbance bands are observed for condensed films of several dyes, which are assigned to H aggregates (planar pincushion-like arrangement of the chromophores). By means of mol. models several mol. arrangements are discussed which are consistent with the exptl. results. Numerous synthetic intermediates are included in the present paper. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Formula: C8H6N2O2).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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. Formula: C8H6N2O2

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Synthesis of Densely Substituted Pyridine Derivatives from 1-Methyl-1,3-(ar)enynes and Nitriles by a Formal [4+2] Cycloaddition Reaction was written by He, Dandan;Wang, Bowen;Duan, Kanghui;Zhou, Yang;Li, Meng;Jiang, Huanfeng;Wu, Wanqing. And the article was included in Organic Letters in 2022.Application In Synthesis of 3-(tert-Butyl)benzonitrile This article mentions the following:

An attractive method for assembling densely substituted pyridine derivatives I [R = Ph, 4-MeC₆H₄, 2-naphthyl, etc.; R¹ = H, 6-Me, 6-Ph, 7-Ph, 8-F; R² = H, Me, CN, Ph; R³ = Ph, 4-FC₆H₄, 2-pyridyl, etc.], II [R⁴ = Ph, 4-MeOC₆H₄, 3-ClC₆H₄, etc.; R⁵ = Ph, 2-naphthyl, 2-pyridyl, etc.; Y = O, S], III [R⁶ = H, 3-Me, 4-MeO, etc.] from 1-methyl-1,3-(ar)enynes and nitriles via a formal [4+2] cycloaddition had been established. The well-balanced affinities of two alkali metal salts enabled C(sp³)-H bond activation and excellent chemo- and regioselectivities. Exptl. studies revealed that nitrile functioned only as a partial nitrogen source for pyridine synthesis, and the addition of a metalated imine intermediate to an intramol. alkyne was the rate-limiting step. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Application In Synthesis of 3-(tert-Butyl)benzonitrile).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) 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. 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-(tert-Butyl)benzonitrile

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A simple triazine (D-A) based organic fluorophore selective dual sensor for Copper(II) and dichromate ions and its solvatochromism, solid state sensing, logic gate applications was written by Harikrishnan, Muniyasamy;Sadhasivam, Velu;Mariyappan, Mathappan;Murugesan, Sepperumal;Malini, Nelson;Siva, Ayyanar. And the article was included in Dyes and Pigments in 2019.Name: 4-(Ethylamino)benzonitrile This article mentions the following:

Herein, the design and synthesis of triazine based fluorophore for selective dual sensing of copper(II) and dichromate ions in non-aqueous solution has been reported. The triazine based fluorophore (TZAS) was synthesized in very good yield from inexpensive starting materials. The fluorophore has been thoroughly characterized by various spectral techniques. The TZAS has N-(ethyl)amine and triazine core which are acting as donor and acceptor, resp. Further, its interaction with various analytes in both solid and solution phases are studied. The TZAS compound shows pos. solvatochromism upon increasing the solvent polarity from non-polar to polar solvent. The sensing ability of TZAS has been studied against various analytes (cations and anions). The results indicated that the detection limits for dichromate and copper ions in dimethylsulfoxide solvent medium are 1.3 × 10^-8 M and 11 × 10^-8 M resp. The sensing mechanism of the proposed probe in the presence of the Cu²⁺/Cr₂O^2-₇ were determined by the support of NMR, ESI-MS, FTIR spectra, Job’s plot and d. functional theory. Furthermore, the energy gap between frontier orbitals of TZAS and TZAS-analyte calculated through theor. (DFT) anal. The sensing performance of the TZAS is also examined in a logic circuit. This is the first dual coupled sensor of copper(II) cation and dichromate anion by organic fluorophore material. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Name: 4-(Ethylamino)benzonitrile).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) 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).Name: 4-(Ethylamino)benzonitrile

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Synthesis and antimicrobial evaluation of new 4-{[(aryl)methylene]amino}-2-methyl-5,6-substituted thieno[2,3-d]pyrimidines was written by Naresh, K.;Rajeshwar, Y.;Jayaveera, K. N.. And the article was included in World Journal of Pharmacy and Pharmaceutical Sciences in 2014.Application of 70291-62-2 This article mentions the following:

A new series of 4-{[(aryl)methylene]amino}-2-methyl-5,6-substituted thieno[2,3-d]pyrimidines I (R₁R₂ = (CH₂)₃, (CH₂)₅; Ar = C₆H₅, 4-ClC₆H₄, 4-BrC₆H₄, 3-indolyl, etc.) was synthesized by the condensation of 4-amino-2,5,6-substituted theino[2,3-d]pyrimidines II with nine aromatic aldehydes. The compounds were further evaluated for the antibacterial and antifungal activity employing disk diffusion method. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Application of 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application of 70291-62-2

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Discovery, Optimization, and in Vivo Evaluation of Benzimidazole Derivatives AM-8508 and AM-9635 as Potent and Selective PI3Kδ Inhibitors was written by Shin, Youngsook;Suchomel, Julia;Cardozo, Mario;Duquette, Jason;He, Xiao;Henne, Kirk;Hu, Yi-Ling;Kelly, Ron C.;McCarter, John;McGee, Lawrence R.;Medina, Julio C.;Metz, Daniela;San Miguel, Tisha;Mohn, Deanna;Tran, Thuy;Vissinga, Christine;Wong, Simon;Wannberg, Sharon;Whittington, Douglas A.;Whoriskey, John;Yu, Gang;Zalameda, Leeanne;Zhang, Xuxia;Cushing, Timothy D.. And the article was included in Journal of Medicinal Chemistry in 2016.COA of Formula: C5H3ClN4 This article mentions the following:

Lead optimization efforts resulted in the discovery of two potent, selective, and orally bioavailable PI3Kδ inhibitors, 1 (AM-8508) and 2 (AM-9635), with good pharmacokinetic properties. The compounds inhibit B cell receptor (BCR)-mediated AKT phosphorylation (pAKT) in PI3Kδ-dependent in vitro cell based assays. These compounds which share a benzimidazole bicycle are effective when administered in vivo at unbound concentrations consistent with their in vitro cell potency as a consequence of improved unbound drug concentration with lower unbound clearance. Furthermore, the compounds demonstrated efficacy in a Keyhole Limpet Hemocyanin (KLH) study in rats, where the blockade of PI3Kδ activity by inhibitors 1 and 2 led to effective inhibition of antigen-specific IgG and IgM formation after immunization with KLH. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4COA of Formula: C5H3ClN4).

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

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Discovery of Tetrasubstituted Imidazolines as Potent and Selective Neuropeptide Y Y5 Receptor Antagonists: Reduced Human Ether-a-go-go Related Gene Potassium Channel Binding Affinity and Potent Antiobesity Effect was written by Sato, Nagaaki;Ando, Makoto;Ishikawa, Shiho;Jitsuoka, Makoto;Nagai, Keita;Takahashi, Hirobumi;Sakuraba, Aya;Tsuge, Hiroyasu;Kitazawa, Hidefumi;Iwaasa, Hisashi;Mashiko, Satoshi;Gomori, Akira;Moriya, Ryuichi;Fujino, Naoko;Ohe, Tomoyuki;Ishihara, Akane;Kanatani, Akio;Fukami, Takehiro. And the article was included in Journal of Medicinal Chemistry in 2009.Name: 4-methoxypicolinonitrile This article mentions the following:

A series of novel imidazoline derivatives was synthesized and evaluated as neuropeptide Y (NPY) Y5 receptor antagonists. Optimization of previously reported imidazoline leads, I and II, was attempted by introduction of substituents at the 5-position on the imidazoline ring and modification of the bis(4-fluorophenyl) moiety. A number of potent derivatives without human ether-a-go-go related gene potassium channel (hERG) activity were identified. Selected compounds, including III, were shown to have excellent brain and CSF permeability. Compound III displayed a suitable pharmacokinetic profile for chronic in vivo studies and potently inhibited D-Trp³⁴NPY-induced acute food intake in rats. Oral administration of III resulted in a potent reduction of body weight in a diet-induced obese mouse model. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Name: 4-methoxypicolinonitrile).

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. 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.Name: 4-methoxypicolinonitrile

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Nitrile – Wikipedia,
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