Category: nitriles-buliding-blocks

Ligand-Promoted Non-Directed C-H Cyanation of Arenes was written by Liu, Luo-Yan;Yeung, Kap-Sun;Yu, Jin-Quan. And the article was included in Chemistry – A European Journal in 2019.Quality Control of 3-(tert-Butyl)benzonitrile This article mentions the following:

The first example of a 2-pyridone accelerated non-directed C-H cyanation with an arene as the limiting reagent was reported. This protocol was compatible with a broad scope of arenes, including advanced intermediates, drug mols. and natural products. A kinetic isotope experiment (k_H/k_D=4.40) indicated that the C-H bond cleavage is the rate-limiting step. Also, the reaction is readily scalable, further showcasing the synthetic utility of this method. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Quality Control of 3-(tert-Butyl)benzonitrile).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Quality Control of 3-(tert-Butyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Silver co-ordination compounds with aliphatic nitriles containing amino nitrogen as H bond donor or additional metal binding site: formation of a ring, a chain, a polymeric sheet and a 3D polymeric channeled structure was written by Erxleben, Andrea. And the article was included in CrystEngComm in 2002.HPLC of Formula: 7528-78-1 This article mentions the following:

Three coordination polymers and a discrete 20-membered macrometallacycle were prepared by crystallization of Ag salts with the conformationally flexible, polyfunctional ligands N-(2-cyanoethyl)glycine (ceg), 3,3-iminodipropionitrile (idpn) and tris(2-cyanoethyl)amine (tca). Single-crystal x-ray analyses of [Ag₂(tca)₂](ClO₄)₂ (1), [Ag(idpn)]ClO₄ (2), [Ag(ceg)]CF₃SO₃ (3) and [Ag(ceg)]ClO₄·0.5H₂O (4) revealed a bimetallic macrocycle (1), a 2-dimensional sheet structure with 4.8² topol. (2), a 3-dimensional network structure with rhomboid channels (3) and a 1-dimensional chain structure (4). The rhomboid channels in 3 are generated by 36-membered macrometallacyclic subunits consisting of four Ag atoms and four ceg ligands with ceg binding through the carboxylate group and the nitrile N. The amino N of ceg is protonated and serves as a H bond donor for the triflate anions that are incorporated into the macrocycles, thus stabilizing the channeled structure. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1HPLC of Formula: 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).HPLC of Formula: 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

New heterocyclic Meisenheimer complexes. Action of methoxide and hydride ions on 2,4-substituted thiophenes and selenophenes was written by Paulmier, Claude;Simonnin, Marie Paule;Chatrousse, Alain Pierre;Terrier, Francois. And the article was included in Tetrahedron Letters in 1973.Electric Literature of C5H2N2O2S This article mentions the following:

Meisenheimer complexes, formed by addition of MeOK to 2,4-disubstituted thiophenes and selenophenes (I; X = S, Se; R, R1 = NO2, CN), were assigned structure II (R2 = OMe) from NMR data. Addition of Me4NBH4 to I (X = S; R = NO2, CN, R1 = NO2) gave analogous II (R = NO2, CN; R1 = NO2; R2 = H), but with I (X = S, R = NO2, R1 = CN; X = Se, R, R1 = NO2, CN) ring-opening occurred. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Electric Literature of C5H2N2O2S).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Electric Literature of C5H2N2O2S

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity was written by Du, Tian;Wang, Biwen;Wang, Chao;Xiao, Jianliang;Tang, Weijun. And the article was included in Chinese Chemical Letters in 2021.Related Products of 101219-69-6 This article mentions the following:

A chiral cobalt pincer complex, when combined with an achiral electron-rich mono-phosphine ligand, catalyzes efficient asym. hydrogenation of a wide range of aryl ketones, affording chiral alcs. with high yields and moderate to excellent enantioselectivities (29 examples, up to 93% ee). Notably, the achiral mono-phosphine ligand showed a remarkable effect on the enantioselectivity of the reaction. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Related Products of 101219-69-6).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. 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.Related Products of 101219-69-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Dissociative ionization of 7-dialkylaminocoumarins under electron impact was written by Gorozhankin, S. K.;Kirpichenok, M. A.;Klyuev, N. A.;Zhil’nikov, V. G.. And the article was included in Izvestiya Timiryazevskoi Sel’skokhozyaistvennoi Akademii in 1987.Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

The behavior of 19 substituted 7-aminocoumarins, eg, I (R = OEt, CF₃, R¹ = H; R = Me, R¹ = thiocyanato; R = CF₃, R¹ = cyano), II (R = Ac, R¹ = H; R = H, R¹ = Cl), and III (R = Me, R¹ = H, CH₂CO₂Et; R = H, R¹ = CO₂ Et; R = CF₃, R¹ = H), under electron impact mass spectroscopic conditions was studied. The pyrone ring in I–III was more stable to degradation than in other coumarins. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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.Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A transient outward potassium current activator recapitulates the electrocardiographic manifestations of Brugada syndrome was written by Calloe, Kirstine;Cordeiro, Jonathan M.;Di Diego, Jose M.;Hansen, Rie S.;Grunnet, Morten;Olesen, Soren Peter;Antzelevitch, Charles. And the article was included in Cardiovascular Research in 2009.Computed Properties of C7H4Br2N2 This article mentions the following:

Aims: Transient outward potassium current (I_to) is thought to be central to the pathogenesis of the Brugada syndrome (BrS). However, an I_to activator has not been available with which to validate this hypothesis. Here, we provide a direct test of the hypothesis using a novel I_to activator, NS 5806 (I). Methods and results: Isolated canine ventricular myocytes and coronary-perfused wedge preparations were used. Whole-cell patch-clamp studies showed that I (10 μM) increased peak I_to at +40 mV by 79 ± 4% (24.5 ± 2.2 to 43.6 ± 3.4 pA/pF, n = 7) and slowed the time constant of inactivation from 12.6 ± 3.2 to 20.3 ± 2.9 ms (n = 7). The total charge carried by I_to increased by 186% (from 363.9 ± 40.0 to 1042.0 ± 103.5 pA·ms/pF, n = 7). In ventricular wedge preparations, I increased phase 1 and notch amplitude of the action potential in the epicardium, but not in the endocardium, and accentuated the ECG J-wave, leading to the development of phase 2 re-entry and polymorphic ventricular tachycardia (n = 9). Although sodium and calcium channel blockers are capable of inducing BrS only in right ventricular (RV) wedge preparations, the I_to activator was able to induce the phenotype in wedges from both ventricles. I induced BrS in 4/6 right and 2/10 left ventricular wedge preparations Conclusion: The I_to activator I recapitulates the electrog. and arrhythmic manifestation of BrS, providing evidence in support of its pivotal role in the genesis of the disease. Our findings also suggest that a genetic defect leading to a gain of function of I_to could explain variants of BrS, in which ST-segment elevation or J-waves are evident in both right and left ECG leads. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Computed Properties of C7H4Br2N2).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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.Computed Properties of C7H4Br2N2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A new synthesis of benzo[b]thiophenes and benzo[c]thiophenes by annulation of disubstituted thiophenes was written by Terpstra, Jan W.;Van Leusen, Albert M.. And the article was included in Journal of Organic Chemistry in 1986.Computed Properties of C6H5NS This article mentions the following:

Nine newly prepared ortho-disubstituted thiophenes I (R = CHO, CO₂Me, cyano; n = 1, 2) and II (R = CO₂Me, cyano, n = 1, 2) react with Michael acceptors to form benzo[b]-, e.g. III, and benzo[c]thiophenes, e.g. IV. This novel annulation process is specifically suited to form benzothiophenes with substituents in the benzene moiety. Substitution patterns so obtained are uncommon and difficultly accessible otherwise; none of the 31 benzothiophenes described in this paper were reported previously. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Computed Properties of C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Computed Properties of C6H5NS

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Site-selectivity in the cyanation of 3-substituted pyridine 1-oxides with trimethylsilanecarbonitrile was written by Sakamoto, Takao;Kaneda, Sohichi;Nishimura, Sumiko;Yamanaka, Hiroshi. And the article was included in Chemical & Pharmaceutical Bulletin in 1985.Quality Control of 4-methoxypicolinonitrile This article mentions the following:

Treatment of pyridine 1-oxides I (R = Br, Cl, F, OMe, NMe₂, Me, Et, Ph, CONEt₂, CO₂Et, cyano) with Me₃SiCN gave 2- and 6-cyanopyridines II and III. The II – III ratio was strongly influenced by R, with II being the only product when R = F, OMe, NMe₂. Nitropyridine 1-oxides underwent deoxygenation but not cyanation with Me₃SiCN. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Quality Control of 4-methoxypicolinonitrile).

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. 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.Quality Control of 4-methoxypicolinonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent was written by Dohi, Toshifumi;Ito, Motoki;Yamaoka, Nobutaka;Morimoto, Koji;Fujioka, Hiromichi;Kita, Yasuyuki. And the article was included in Tetrahedron in 2009.Formula: C6H5NS This article mentions the following:

Bithiophenes and bipyrroles are prepared regioselectively by oxidative coupling reactions of thiophenes and pyrroles mediated by hypervalent iodine reagents such as PhI(O₂CCF₃)₂ (PIFA) in the presence of Lewis acids. Substituted thiophenes and thiophenecarbonitriles, pyrrolecarbonitriles, and indolecarbonitriles are prepared by oxidative substitution reactions of thiophenes, N-tosylpyrroles, and N-tosylindoles with PIFA in the presence of boron trifluoride etherate and nucleophiles such as trimethylsilyl cyanide. (thienyl)aryliodonium salts are prepared by reaction of 3-methylthiophene with either PIFA or with iodosobenzene and acids or by reactions of (hydroxy)aryliodonium tosylates with thiophenes in 2,2,2-trifluoroethanol. All of the above reactions are proposed to occur via single-electron oxidation of the substrates with hypervalent iodine reagents. The paper is preceded by a review of the work of the Kita research group on oxidative cyclizations and intramol. oxidative coupling reactions of arenes mediated by hypervalent iodine reagents. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Formula: C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Formula: C6H5NS

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Basic Ionic Liquid [bmIm]OH-Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes was written by Kaki, Venkata Rao;Akkinepalli, Raghuram Rao;Deb, Pran Kishore;Pichika, Mallikarjuna Rao. And the article was included in Synthetic Communications in 2015.Application In Synthesis of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

A simple, efficient, and environmentally friendly procedure was developed based on the Gewald reaction for the synthesis of 2-aminothiophenes using a basic ionic liquid [bmIm]OH as both catalyst and solvent. Besides being a green protocol, the method offers advantages of successful synthesis of a variety of alkyl, aryl, alkoxy, and alkylamino-2-aminothiophenes in good yields. 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 In Synthesis 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. 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 In Synthesis of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts