Month: January 2023

Regiocontrolled Remote C-H Olefination of Small Heterocycles was written by Achar, Tapas Kumar;Ramakrishna, Kankanala;Pal, Tapas;Porey, Sandip;Dolui, Pravas;Biswas, Jyoti Prasad;Maiti, Debabrata. And the article was included in Chemistry – A European Journal in 2018.Related Products of 60979-25-1 This article mentions the following:

Achieving site-selective C-H functionalization of arene is a fundamental challenge, as it is mainly controlled by the electronic nature of the mols. A chelation-assisted C-H functionalization strategy overcomes the selectivity issues by utilizing distance and geometry of covalently attached directing groups (DGs). This strategy requires stoichiometric DG installation/removal and a suitable functional group on which to tether the DG. Such strategies are ineffective for small heterocycles unless suitable functional groups are added. Moreover, heterocycles are not the judicious choice as substrates owing to the possibilities of catalyst deactivation. Inspired by recent developments, this work demonstrates the utilization of a chelating template backbone bearing covalently attached directing groups, which enables site-selective remote C-H functionalization of heterocycles. The observed selectivity is the outcome of non-covalent interactions between the heterocycles and bifunctional template backbone. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Related Products of 60979-25-1).

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. 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.Related Products of 60979-25-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A Highly Active Palladium Catalyst for Intermolecular Hydroamination. Factors that Control Reactivity and Additions of Functionalized Anilines to Dienes and Vinylarenes was written by Johns, Adam M.;Utsunomiya, Masaru;Incarvito, Christopher D.;Hartwig, John F.. And the article was included in Journal of the American Chemical Society in 2006.COA of Formula: C14H12N2 This article mentions the following:

We report a catalyst for intermol. hydroamination of vinylarenes that is substantially more active for this process than catalysts published previously. With this more reactive catalyst, we demonstrate that additions of amines to vinylarenes and dienes occur in the presence of potentially reactive functional groups, such as ketones with enolizable hydrogens, free alcs., free carboxylic acids, free amides, nitriles, and esters. The catalyst for these reactions is generated from [Pd(η³-allyl)Cl]₂ (with or without added AgOTf) or [Pd(CH₃CN)₄](BF₄)₂ and Xantphos (9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene), which generates complexes with large P-Pd-P bite angles. Studies on the rate of the C-N bond-forming step that occurs by attack of amine on an η³-phenethyl and an η³-allyl complex were conducted to determine the effect of the bite angle on the rate of this nucleophilic attack. Studies on model η³-benzyl complexes containing various bisphosphines showed that the nucleophilic attack was faster for complexes containing larger P-Pd-P bite angles. Studies of substituted unsym. and unsubstituted sym. model η³-allyl complexes showed that nucleophilic attack on complexes ligated by Xantphos was faster than on complexes bearing ligands with smaller bite angles and that nucleophilic attack on unsym. allyl complexes with larger bite angle ligands was faster than on unsym. allyl complexes with smaller bite angle ligands. However, monitoring of catalytic reactions of dienes by ³¹P NMR spectroscopy showed that the concentration of active catalyst was the major factor that controlled rates for reactions of sym. dienes catalyzed by complexes of phosphines with smaller bite angles. The identity of the counterion also affected the rate of attack:reactions of allylpalladium complexes with chloride counterion occurred faster than reactions of allylpalladium complexes with triflate or tetrafluoroborate counterion. As is often observed, the dynamics of the allyl and benzyl complexes also depended on the identity of the counterion. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3COA of Formula: C14H12N2).

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. 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. COA of Formula: C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Acid anilides. XII. Preparation of 4- and 5-hydroxyalkananilides from γ- and δ-lactones was written by de Jonge, A. P.;van der Ven, B.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas in 1965.HPLC of Formula: 4714-63-0 This article mentions the following:

The synthesis of a series of RCH(OH)(CH₂)_nCONHPh (I) (n = 2 or 3) from less than 10 mg. of the corresponding lactones is described. EtBr (1.5 cc.) in 15 cc. dry Et₂O added dropwise to 480 mg. Mg and 5 cc. dry Et₂O at such a rate as to maintain refluxing and diluted with Et₂O to 25 cc., a 1-cc. portion added dropwise to 1 cc. solution of 77 mg. PhNH₂/cc. C₆H₆, and the mixture treated with not more than 10 mg. lactone in dry Et₂O, refluxed 1.5 hrs. under an air condenser until the Et₂O had evaporated, and treated with 10 cc. Et₂O and 2 cc. 3N HCl gave the corresponding I. In this manner were prepared the following I (n = 2) (R and m.p. given): Bu, 114.9-15.8° (Et₂O-petr. ether); iso-Bu, 137.6-8.9° (Et₂O-petr. ether); Am (II), 99.5-100° (Et₂O-petr. ether); C₆H₁₃ (III), 105.2-5.9° (50% EtOH); C₇H₁₅, 106-7° (Et₂O-petr. ether); C₈H₁₇, 108.6-9.6° (50% EtOH). Similarly were prepared the following I (n = 3) (same data given): Pr (IV), 100.9-1.4° (Et₂O-petr. ether); iso-Pr, 92.1-3.2° (Et₂O-petr. ether); Bu, 102.2-3.3° (Et₂O-petr. ether); Am (V), 101.3-1.9° (Et₂O-petr. ether); iso-Am, 102.7-3.8° (Et₂O-petr. ether); C₆H₁₃, 96.4-7.6° (Et₂O); C₇H₁₅ (VI), 104.4-5.3° (Et₂O-petr. ether); C₈H₁₇, 98.0-9.1° (Et₂O); C₉H₁₉, 100.6-1.4° (Et₂O-petr. ether); C₁₀H₂₄, 103.3-4.1° (Et₂O). The rates of the hydrolysis of II, III, IV, and V in 3N HCl were measured spectrophotometrically at 241 mμ; about 8.5 mg. appropriate I in 50 cc. 30% aqueous MeOH was treated with 7 cc. 3.25N HCl; the rate constants k min.^-1 and the half-life period in min. were for the following compounds: II, 0.0271, 25.6; III, 0.0292, 23.7; IV, 0.0189, 36.6; V, 0.0184, 37.7. The solubility of V in cyclohexane at 20° was 43.6 mg./l., that of VI 40.2 mg./l. 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. 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.HPLC of Formula: 4714-63-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Preparation of Quinazolinoquinazolinones via a Cascade Approach was written by Ramanathan, Mani;Liu, Shiuh-Tzung. And the article was included in Journal of Organic Chemistry in 2018.Safety of 2-Amino-3-chlorobenzonitrile This article mentions the following:

A one-pot synthesis of quinazolino[3,4-a]quinazolin-13-ones was realized from the direct reaction of o-(methoxycarbonyl)benzenediazonium salts, nitriles, and 2-cyanoanilines in moderate to good yields. This method utilizes the in situ generation of reactive N-arylnitrilium ion, which undergoes further amination/tandem cyclization/amidation to deliver the desired polycyclic scaffolds with consecutive formation of four N-C bonds. Flexibility in substitution patterns, mild reaction conditions, and operational simplicity are the salient features of this methodol. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Safety of 2-Amino-3-chlorobenzonitrile).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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.Safety of 2-Amino-3-chlorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Second-order nonlinear optical properties of new organic conjugated molecules was written by Kawabe, Y.;Ikeda, H.;Sakai, T.;Kawasaki, K.. And the article was included in Journal of Materials Chemistry in 1992.Computed Properties of C18H10N2 This article mentions the following:

Both real and imaginary parts of the second-order nonlinear optical coefficients for a wide range of new organic conjugated materials were measured. The technique of elec.-field-induced second-harmonic generation to determine the optical nonlinearity is described for materials highly absorptive at the harmonic wavelength. The authors evaluated the mol. nonlinear optical coefficients of nitro compounds and aldehydes, barbituric acid derivatives, fulvene derivatives, chalcone derivatives, retinal derivatives, Schiff base compounds, and fused-ring mols., at 1.064 μm. Among these materials, nitro mols. and Schiff base compounds had large optical nonlinearities and good transparency at visible wavelengths. Barbituric acid derivatives and retinal derivatives also had large nonlinearities, but displayed strong absorption of the harmonics. A large enhancement of nonlinearities was achieved in fulvene derivatives by extending the conjugated chains. S atoms, non-benzoic conjugated systems, and fused rings contributed to nonlinear optical effects. Several mols. had very large second-order optical nonlinearities; the products of the mol. nonlinearities and permanent dipole moments μ₀β of these were of the order of 10^-45-10^-44 esu. The relations between mol. nonlinearity and absorption peak energy are discussed. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Computed Properties of C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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 addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Computed Properties of C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts