Nitriles-buliding-blocks

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

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

One-Pot Synthesis of Spirocyclopenta[a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization was written by Li, Quanzhe;Liu, Jiaxin;Wei, Yin;Shi, Min. And the article was included in Journal of Organic Chemistry in 2020.Safety of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramol. Friedel-Crafts-type cyclization from propargyl alc.-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Safety of 2-Amino-4-(trifluoromethyl)benzonitrile).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Organorhodium-Functionalized Periodic Mesoporous Organosilica: High Hydrophobicity Promotes Asymmetric Transfer Hydrogenation in Aqueous Medium was written by Liu, Rui;Jin, Ronghua;Kong, Lingyu;Wang, Jinyu;Chen, Chen;Cheng, Tanyu;Liu, Guohua. And the article was included in Chemistry – An Asian Journal in 2013.Name: (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

Three organosilica-bridged periodic mesoporous organosilicas were prepared by the immobilization of a chiral N-sulfonylated diamine-based organorhodium complex within their silicate network. Structural anal. and characterization confirmed their well-defined single-site active rhodium centers, while electron microscopy revealed their highly ordered hexagonal mesostructures. Among these three different organosilica-bridged periodic mesoporous organosilicas, the ethylene-bridged periodic mesoporous organosilica catalyst exhibited excellent heterogeneous catalytic activity and high enantioselectivity in the aqueous asym. transfer hydrogenation of aromatic ketones. This superior catalytic performance was attributed to its salient hydrophobicity, while its comparable enantioselectivity relative to the homogeneous catalyst was derived from the confined nature of the chiral organorhodium catalytic sites. Furthermore, this ethylene-bridged periodic mesoporous organosilica could be conveniently recovered and reused at least 12 times without the loss of its catalytic activity. This feature makes this catalyst attractive for practical organic synthesis in an environmentally friendly manner. This study offers a general way of optimizing the bridged organosilica moiety in periodic mesoporous organosilicas, thereby enhancing its catalytic activity in heterogeneous catalysis. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Name: (R)-4-(1-Hydroxyethyl)benzonitrile).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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 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: (R)-4-(1-Hydroxyethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Density function theory study on anthracene substituted by dicyanovinyl in different positions was written by Zhang, Jinglai;Miao, Tifang;Wang, Hua;Tian, Anmin. And the article was included in Huaxue Tongbao in 2003.Application of 55490-87-4 This article mentions the following:

Results of RHF(RHF) and d. function theory(DFT) calculations are reported for 2-dicyanovinyl anthracene(2-DCVA) and 9-dicyanovinyl anthracene(9-DCVA) at B3LYP/6-311+G(d,p)//RHF/6-31G(d,p) level. The equilibrium geometries of 2-DCVA and 9-DCVA have been optimized and the harmonic vibrational frequencies have been calculated The calculating results show that the ground state of 9-DCVA is higher than that of 2-DCVA in total energy. Having revolved angles between anthracene and dicyanovinyl from -180.0° to 180.0°, their potential energy curves are obtained to find their equilibrium geometries, The results show that there are two different stable geometries in energy and a transition geometry for 2-DCVA while there are a stable geometry and two transition geometries for 9-DCVA, the structure of 2-DCVA is more planar than 9-DCVA. At PM3/CIS level, their electronic spectrum were calculated and the vertical excitation energies and corresponding oscillator strengths from the ground states to the excited states are obtained. These results are in good agreement with the results obtained from experiment In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Application of 55490-87-4).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis, characterization, and antibacterial and anti-inflammatory activities of new pyrimidine and thiophene derivatives was written by Lahsasni, Siham;Al-Hemyari, Dunya A. M.;Ghabbour, Hazem A.;Mabkhoot, Yahia Nasser;Aleanizy, Fadilah S.;Alothman, Asma A.;Almarhoon, Zainab M.. And the article was included in Journal of Chemistry in 2018.Electric Literature of C8H8N2S This article mentions the following:

Substituted[4,5]thieno[2,3-d]thiazolo[3,2-a]pyrimidin-5-ones and pyrimidin-5(6H)-imines, compounds I [X = O, NH; Y = (CH₂)_n; n = 1-3] were synthesized via reaction of the starting compounds, Et 2-amino-substituted[b]thiophene-3-carboxylates and 2-amino-substituted [b]thiophene-3-carbonitriles, resp., with 2-bromothiazole. Synthesis of (bromo-substituted[b]thiophen-2-yl) alkanamides, compds II [R = CN, COOEt; Z = (CH₂)_m; n = 1-3; m = 3, 4] and thieno[2,3-d][1,3]oxazin-4-imine was accomplished via reaction of the starting compounds with bromoalkyl chloride through nucleophilic substitution; however, for the synthesis of this compound, nucleophilic substitution was followed by nucleophilic addition to a nitrile group to form the oxazinimine ring. 1-(3-Cyano-substituted[b]thiophen-2-yl)-3-(4-(trifluoromethyl)phenyl)thioureas, compound III [n = 1-3] were obtained via reaction of the starting compounds and 4-(trifluoromethyl phenyl)isothiocyanate. The lead compounds rapidly reacted with 4-(trifluoromethyl)benzaldehyde or 4-(2-pyridyl)benzaldehyde in acidic medium to yield compounds IV [R¹ = CF₃, 2-pyridyl, n = 1-3] in large quantities. X-ray crystallog. of compounds II [R = CN, n = 3] and IV [R¹ = CF₃, n = 3] confirmed their structures. Antimicrobial studies revealed that compound III [n = 1] was equally potent to ampicillin against Bacillus strains. Moreover, compounds I [X = NH, n = 3], II [R = COOEt, n = 3], and III [n = 1] possessed greater anti-inflammatory potency than that of the standard drug. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Electric Literature of C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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. 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.Electric Literature of C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The [CoN₄(OH)(OH₂)]²⁺ (N₄ = trpn, cyclen and tren) promoted hydrolysis of the phosphotriester 2,4-dinitrophenyl diethyl phosphate was written by Hay, Robert W.;Govan, Norman. And the article was included in Transition Metal Chemistry (Dordrecht, Netherlands) in 1998.Reference of 7528-78-1 This article mentions the following:

The [CoL(OH₂)₂]³⁺ (L = trpn, cyclen and tren) promoted hydrolysis of the phosphotriester 2,4-dinitrophenyl di-Et phosphate to give di-Et phosphate and 2,4-dinitrophenolate was studied in detail over the pH range 3-7.5. The pK values of the various complexes were determined at 25° and I = 0.1 mol dm^-3 by potentiometric titration The pH-rate profiles for the reactions are consistent with the hydroxoaqua complex [CoL(OH)(OH₂)]²⁺ being the active species in the hydrolysis. No evidence for saturation kinetics was obtained and values of k_cat determined at pH 7 and 25° (I = 0.1 mol dm^-3) are 4.24 × 10^-3 dm³ mol^-1 s^-1 (tren) < 3.05 × 10^-2 dm³ mol^-1 s^-1 (cyclen) < 7.5 × 10^-1 dm³ mol^-1 s^-1 (trpn). Studies involving the more reactive phosphonate ester 2,4-dinitrophenyl Et methylphosphonate suggest that the rate-determining step in the reaction is the decomposition of the ternary complex between the Co(III) complex and the phosphotriester. The rate enhancement using 0.01 mol dm^-3 Co(trpn)³⁺ is some 4.6 × 10⁴ fold at pH 7 and 25°. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Reference 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.Reference of 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts