Month: February 2023

Synthesis of Secondary Amines from One-Pot Reductive Amination with Formic Acid as the Hydrogen Donor over an Acid-Resistant Cobalt Catalyst was written by Jiang, Liang;Zhou, Peng;Zhang, Zehui;Jin, Shiwei;Chi, Quan. And the article was included in Industrial & Engineering Chemistry Research in 2017.Synthetic Route of C14H12N2 This article mentions the following:

Developing new heterogeneous non-noble metal catalysts to replace noble-metal catalysts in organic transformations is of high importance in modern synthetic chem. Herein, nitrogen-doped carbon embedded Co catalysts (abbreviated as Co@CN-T-AT, in which T represents the pyrolysis temperature, AT represents the acid-leaching process) were prepared through the simple pyrolysis of graphene oxide-supported cobalt-based zeolitic imidazolate-frameworks, followed by the acid-leaching process. The Co@CN-600-AT catalyst demonstrated the highest catalytic activity among the synthesized Co catalyst toward the reductive amination of carbonyl compounds with nitro compounds by transfer hydrogenation with formic acid as the hydrogen donor, which integrated three consecutive steps into a one-pot reaction. By applying this catalyst, structurally diverse secondary amines were produced in good to excellent yields without the reduction of other functional groups. The transfer hydrogenation of the imines (C=N bonds) was the rate-determining step. Furthermore, the catalyst was highly stable and could be reused without decrease of the catalytic activity. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Synthetic Route of 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Synthetic Route of C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liquid-crystalline compounds. X. trans-4-Cyanocyclohexanol derivatives with liquid-crystalline properties was written by Praefcke, Klaus;Schmidt, Dietmar. And the article was included in Chemiker-Zeitung in 1981.HPLC of Formula: 24056-34-6 This article mentions the following:

Nine trans-4-cyanocyclohexyl esters (I and II, R¹ = C₅H₁₁, C₇H₁₅, C₉H₁₉; and III, R² = Pr, C₅H₁₁, C₇H₁₅) were prepared by converting the appropriate carboxylic acids into their acid chlorides and esterifying them with trans-4-cyanocyclohexanol; the esters exhibited both nematic and isotropic liquid crystal phases. cis-4-Cyanocyclohexyl trans–p-(4-propylcyclohexyl)benzoate, which showed a nematic phase, was prepared similarly. In the experiment, the researchers used many compounds, for example, 4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6HPLC of Formula: 24056-34-6).

4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).HPLC of Formula: 24056-34-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A high-yielding preparation of β-keto nitriles was written by Ji, Yaohui;Trenkle, William C.;Vowles, James V.. And the article was included in Organic Letters in 2006.HPLC of Formula: 4435-14-7 This article mentions the following:

β-Keto nitriles are important precursors for a wide variety of biol. active heterocycles. A facile procedure for the high-yielding acylation of nitrile anions with unactivated esters to provide β-keto nitriles is reported. Thus, reaction of PhCH₂CH₂CN with PhCO₂Et in THF containing EtCMe₂OH K salt at room temperature for 10 min gave 95% PhCH₂CH(CN)COPh. The procedure is successful with enolizable and nonenolizable esters as well as hindered nitrile anions. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7HPLC of Formula: 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).HPLC of Formula: 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases was written by Thinnes, C. C.;Tumber, A.;Yapp, C.;Scozzafava, G.;Yeh, T.;Chan, M. C.;Tran, T. A.;Hsu, K.;Tarhonskaya, H.;Walport, L. J.;Wilkins, S. E.;Martinez, E. D.;Muller, S.;Pugh, C. W.;Ratcliffe, P. J.;Brennan, P. E.;Kawamura, A.;Schofield, C. J.. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2015.Quality Control of 3-Methylthiophene-2-carbonitrile This article mentions the following:

There is interest in developing potent, selective, and cell-permeable inhibitors of human ferrous iron and 2-oxoglutarate (2OG) oxygenases for use in functional and target validation studies. The 3-component Betti reaction enables efficient one-step C-7 functionalization of modified 8-hydroxyquinolines (8HQs) to produce cell-active inhibitors of KDM4 histone demethylases and other 2OG oxygenases; the work exemplifies how a template-based metallo-enzyme inhibitor approach can be used to give biol. active compounds In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Quality Control of 3-Methylthiophene-2-carbonitrile).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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. 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 3-Methylthiophene-2-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Easy single-step preparation of ZnO nanoparticles by sedimentation method and studying their catalytic performance in the synthesis of 2-aminothiophenes via Gewald reaction was written by Tayebee, Reza;Javadi, Farzad;Argi, Gholamreza. And the article was included in Journal of Molecular Catalysis A: Chemical in 2013.Product Details of 70291-62-2 This article mentions the following:

Zinc oxide is a multi-purpose active material with important catalytic applications. Nano-sized ZnO particles were easily synthesized through sedimentation of zinc acetate di-hydrate in absolute ethanol and were characterized by XRD and SEM. The XRD results indicated pure wurtzite structure with the average particle size of 26.9 nm for the nano-particles. Size of ZnO nano-particles was decreased while solution concentration was increased. This observation would be explained considering enhancing nucleation processes of nano-particles at high concentration of zinc acetate. The prepared nano-particles (2.5 mol%) were used as catalyst for the fast and efficient synthesis of 2-aminothiophenes under solvent free conditions. The three-component mixture of a carbonyl compound, malonodinitrile, and elemental sulfur was converted into the corresponding 2-aminothiophene in moderate to high yields with excellent selectivity. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Product Details of 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Product Details of 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of the C₁-C₁₅ fragment of apicularen A through a regioselective electron-transfer-initiated cyclization reaction was written by Poniatowski, Alexander J.;Floreancig, Paul E.. And the article was included in Synthesis in 2007.COA of Formula: C11H13NO This article mentions the following:

In this paper we report the preparation of the benzyltetrahydropyran fragment I of the vacuolar ATPase inhibitor apicularen A through an oxidative cyclization protocol. In this reaction regioselective cleavage of one homobenzylic ether in the presence of another homobenzylic ether is achieved by selectively weakening one carbon-carbon σ-bond through substitution. This work demonstrates that oxidative fragmentation reactions can be used to generate stable cations selectively, even in the presence of other readily oxidized groups, provided that bond cleavage is sufficiently rapid following oxidation In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5COA of Formula: C11H13NO).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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.COA of Formula: C11H13NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Use of the least squares method for estimating the sorption capability of cyano-group-containing phases in gas chromatography was written by Zakirov, N. S.. And the article was included in Zhurnal Analiticheskoi Khimii in 1987.Formula: C9H12N4 This article mentions the following:

The least squares method was used for quant. estimation of the sorption capability of cyano-group containing stationary phases in gas chromatog. separation of alcs., nitriles, and hydrocarbons. The method can be used for selection and optimization of stationary phases with respect to analyte chain length. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Formula: C9H12N4).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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.Formula: C9H12N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Calcined Mg-Al hydrotalcite as a heterogeneous base catalyst for Gewald aminothiophene synthesis was written by Rajagopal, R.;Jyothi, T. M.;Daniel, Thomas;Srinivasan, K. V.;Rao, B. S.. And the article was included in Synthetic Communications in 2001.COA of Formula: C8H8N2S This article mentions the following:

Calcined Mg-Al hydrotalcite (Mg/Al=4) has been conveniently employed as a heterogeneous base catalyst in the synthesis of 2-amino-3-cyanothiophenes adopting a one pot Gewald aminothiophene methodol. The compounds thus prepared included 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile, 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile, 2-amino-3-cyano-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene and 2-amino-4,5-dimethyl-3-thiophenecarbonitrile. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2COA of Formula: C8H8N2S).

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. 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.COA of Formula: C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Spectroscopic behavior of anthracene substituted by dicyanovinyl in different positions was written by Wang, Hua;Zhang, Baowen;Cao, Yi;Xu, Li. And the article was included in Huaxue Yanjiu in 1997.Electric Literature of C18H10N2 This article mentions the following:

Two conjugating electron donor-acceptor (D-A) compounds, 2-dicyanovinyl anthracene(2-DCVA) and 9-dicyanovinyl anthracene(9-DCVA), were synthesized and their spectroscopic properties in a series of solvents with different polarity and at different temperatures were studied. The results reveal that both compounds show intramol. charge transfer (ICT) state emission at different polarity of solvents and the fluorescence quantum yield (Φ_F) of 2-DCVA is much higher than that of 9-DCVA, due to that the structure of 2-DCVA is more planar than 9-DCVA. The dipole moment differences between excited states and ground states of the both compounds were estimated by the formula of Bilot-Kawski. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Electric Literature of C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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. 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.Electric Literature of C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A recyclable Cu/Al-HT catalyst for amination of aryl chlorides was written by Likhar, Pravin R.;Arundhathi, R.;Kantam, M. Lakshmi. And the article was included in Tetrahedron Letters in 2007.COA of Formula: C14H12N2 This article mentions the following:

A simple Cu/Al-HT catalyzed amination of aryl chlorides with primary and secondary aromatic amines was developed. This ligand-free heterogeneous Cu/Al-HT catalyst, in conjunction with base, also efficiently works for the amination of aryl chlorides with cycloalkyl amines. This method tolerates a variety of functional groups and does not require an expensive additive. 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. 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. 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