Category: nitriles-buliding-blocks

Highly efficient amination in neat water of benzyl chlorides with dialkylformamides catalyzed by N-heterocyclic carbene-palladium(II)-1-methylimidazole complex was written by Chen, Wen-Xin;Zhang, Cai-Yun;Lu, Jian-Mei. And the article was included in Journal of Chemical Research in 2013.Safety of 4-(Morpholinomethyl)benzonitrile This article mentions the following:

N,N-dialkylbenzylamines were synthesized from substituted benzyl chlorides and dialkylformamides in good to almost quant. yields in a eco-friendly solvent, water, in the presence of NHC-Pd(II)-Im complex. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Safety of 4-(Morpholinomethyl)benzonitrile).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) 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.Safety of 4-(Morpholinomethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cyclopropenone-Catalyzed Direct Conversion of Aldoximes and Primary Amides into Nitriles was written by Rai, Ankita;Yadav, Lal Dhar S.. And the article was included in European Journal of Organic Chemistry in 2013.Formula: C6H5NS This article mentions the following:

Efficient conversion of aldoximes and primary amides into nitriles by employing cyclopropenone as an organocatalyst is reported. The reaction proceeds smoothly under mild conditions with 5 mol-% catalyst loading to afford nitriles in excellent yields (78-94 %) in a single operation. This method is equally applicable to both aldoximes and primary amides bearing aromatic, heterocyclic, and aliphatic moieties. The convenient and catalytic procedure widens the scope of the utilization of cyclopropenones in organic synthesis. 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. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Formula: C6H5NS

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Insight into and practical application of pH-controlled asymmetric transfer hydrogenation of aromatic ketones in water was written by Wu, Xiaofeng;Li, Xiaoguang;King, Frank;Xiao, Jianliang. And the article was included in Angewandte Chemie, International Edition in 2005.Application of 101219-69-6 This article mentions the following:

Much faster, more enantioselective, and more-productive catalysis was attained in the asym. transfer hydrogenation of aromatic ketones with the Noyori-Ikariya Ru-Ts-dpen catalyst in water under slightly basic conditions. At low pH values, the reaction was much less efficient and appears to operate through a different mechanism. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Application of 101219-69-6).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Clickable Transformation of Nitriles (RCN) to Oxazolyl Sulfonyl Fluoride Warheads was written by Fang, Wan-Yin;Wang, Shi-Meng;Zhang, Zai-Wei;Qin, Hua-Li. And the article was included in Organic Letters in 2020.COA of Formula: C8H4F3NO This article mentions the following:

The protocol for simple, efficient, and mild synthesis of oxazolyl sulfonyl fluorides was developed through Rh₂(OAc)₄-catalyzed annulation of methyl-2-diazo-2-(fluorosulfonyl)acetate (MDF) or its Et ester derivative with nitriles. This practical method provides a general and direct route to a unique class of highly functionalized oxazolyl-decorated sulfonyl fluoride warheads with great potential in medicinal chem., chem. biol., and drug discovery. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4COA of Formula: C8H4F3NO).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) 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. 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.COA of Formula: C8H4F3NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis, evaluation and structure-activity relationships of 5-alkyl-2,3-dihydroimidazo[1,2-c]quinazoline, 2,3-dihydroimidazo[1,2-c]quinazolin-5(6H)-thiones and their oxo-analogues as new potential bronchodilators was written by Bahekar, Rajesh H.;Rao, A. Raghu Ram. And the article was included in Arzneimittel-Forschung in 2001.Computed Properties of C7H4Br2N2 This article mentions the following:

With an aim to obtain potent bronchodilators, 2 series of 5-alkyl-2,3-dihydroimidazo[1,2-c]quinazolines (Va-1), 2,3-dihydroimidazo[1,2-c]quinazolin-5-(6H)-thiones (VIIIa-d) and their oxo-analogs (IXa-d) were designed. The compounds Va-1 were synthesized by two alternative routes. The former (Method A) based on the dehydrocyclization of 4-(1-hydroxyethyl)aminoquinazoline (IV) and the latter (Method B) involves the usage of 2-aminobenzonitrile (VI) which on reaction with ethylenediamine leads to the formation of the key intermediate 2-(2-aminophenyl)-4,5-dihydro-1H-imidazoles (VII). Finally the intermediate VII on condensation with different acid anhydrides yielded the title compound V. In general, method-A resulted the compound V in quantatively higher yields. 2,3-Dihydroimidazo[1,2-c]quinazolin-5 (6H)-thiones (VIII) were obtained by condensing VIi with carbon disulfide and a further oxidation of VIII gave their corresponding oxo-analogs (IX). The title compounds V, VIII and IX were evaluated for their bronchodilator activity using in vitro and in vivo (standard animal models) methods. All the test compounds exhibited bronchodilator activity. The structure activity relationship studies indicated good correlation between the nature of the substituent and bronchodilator activity. In the 5-alkyl substituted compounds V, a longer alkyl chain showed higher bronchodilator activity. Compounds VIII and IX were less potent and replacement of sulfur with oxygen showed no significant effect on the biol. activity. The presence of halogens altered the biol. activity in both the series. Among the compounds tested, 9-iodo-5-(propyl)-2,3-dihydroimidazo[1,2-c]quinazoline (VI) was the most potent (percentage protection = 87.1%; relative activity = 1.1 compared to the standard aminophylline). 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. 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.Computed Properties of C7H4Br2N2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A comparison of the properties of some 2-aminothiophene-derived disperse dyes was written by Hallas, Geoffrey;Towns, Andrew D.. And the article was included in Dyes and Pigments in 1996.Computed Properties of C12H14N2O4S This article mentions the following:

In the course of an investigation into the properties of monoazo disperse dyes synthesized from aminothiophene diazo components, significant discrepancies were observed between the spectroscopic and fastness data of some thienyl-2-azo dyes compared to that previously reported for closely related analogs. Considerable differences in λ_max and ε_max values were noted; in some cases, light fastness ratings were at variance with previously disclosed figures. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Computed Properties of C12H14N2O4S).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Computed Properties of C12H14N2O4S

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Design, synthesis and biological evaluation of novel 4-(2-fluorophenoxy)quinoline derivatives as selective c-Met inhibitors was written by Wang, Xiaoqiang;Jiang, Nan;Zhao, Sijia;Xi, Shuancheng;Wang, Jiao;Jing, Tongfei;Zhang, Wenyu;Guo, Ming;Gong, Ping;Zhai, Xin. And the article was included in Bioorganic & Medicinal Chemistry in 2017.Name: 2-(Trifluoromethoxy)benzonitrile This article mentions the following:

Two novel series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives bearing 1H-imidazole-4-carboxamido or (E)-3-hydrosulfonylacrylamido motifs were designed, synthesized and evaluated for their in vitro cytotoxic activity. Most of the compounds exhibited moderate to excellent potency against tested three cell lines, and fifteen compounds were further examined for their inhibitory activity against c-Met kinase. The most promising compound I (c-Met kinase [IC₅₀] = 1.1 nM) demonstrated high selectivity and remarkable cytotoxicity against HT-29, MKN-45 and A549 cells with IC₅₀ values of 0.08, 0.22 and 0.07 μM, which were 3.1-, 1.4- and 2.1-fold more active than Foretinib. The preliminary structure-activity relationships as well as mol. docking disclosed that 1H-imidazole-4-carboxamido as a linker was of great importance for the antitumor activity. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4Name: 2-(Trifluoromethoxy)benzonitrile).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) 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. 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.Name: 2-(Trifluoromethoxy)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Selective reduction of α,β-unsaturated nitriles with sodium hydrogen telluride was written by Blay, Gonzalo;Cardona, Luz;Garcia, Begona;Pedro, Jose R.. And the article was included in Synlett in 1995.Formula: C8H13N This article mentions the following:

Sodium hydrogen telluride reacts chemoselectively with α,β-unsaturated nitriles linked to aromatic and aliphatic substituents, e.g., (E)-4-NCC₆H₄CH:CHCN, to give the corresponding saturated nitriles with good yields. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Formula: C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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 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.Formula: C8H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cathodic behaviour of 1-cycloalken-1-yl phenyl sulfones. I. Competition among dimerization, cleavage, isomerization and oligomerization processes in aprotic media was written by Prigent, Sylvie;Cauliez, Pascal;Simonet, Jacques;Peters, Dennis G.. And the article was included in Acta Chemica Scandinavica in 1999.Application of 4435-14-7 This article mentions the following:

1-Cycloalken-1-yl Ph sulfones (1-cyclopenten-1-yl Ph sulfone and 1-cyclohexen-1-yl Ph sulfone) were studied electrochem. in aprotic media (DMF, DMSO, or acetonitrile containing tetraalkylammonium salts) at a mercury electrode. Their behavior was compared with that of 2-norbornen-2-yl Ph sulfone. The expected cleavage reaction is accompanied by a concomitant isomerization process into allyl sulfones that is triggered by electrogenerated bases. A quant. determination of the product distribution during controlled-potential electrolyzes suggests the formation of dimers and oligomeric species, arising through a Michael addition of the sulfone anions to the activated double bond of these sulfones. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Application of 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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 of 4435-14-7

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nucleic acid components and their analogs. CLVIII. Preparation of some substituted 2-amino- and 2-mercaptopyrimidines from trimethinium salts was written by Holy, Antonin;Arnold, Zdenek. And the article was included in Collection of Czechoslovak Chemical Communications in 1973.Reference of 1753-48-6 This article mentions the following:

Condensation of Me2NCR:CR1CH:N(+)Me2(ClO4)(-) (I) (R = H, alkyl, NMe2; R1 = H, alkyl, halo, CN, CO2Et, OCH2Ph) with (H2N)2C:NH or (H2N)2C:S gave II (R2 = NH2) and II (R2 = SH), resp. I (R = H; R1 = OCH2Ph) was prepared from PhCH2OCH2CH(OEt)2 by reaction with ClCH:N(+)Me2Cl(-), hydrolysis, and treatment with Me2NH. I (R = NMe2; R1 = CO2Et) and I (R = NMe2; R1 = CN) were prepared analogously from Me2NCOCH2CO2Et and Me2NCOCH2CN, resp. 5-Methyl-2-pyrimidinone was prepared from II (R = H; R1 = Me; R2 = SH) and ClCH2CO2H. Reaction of II (R = H; R1 = OCH2Ph; R2 = NH2) and II (R = H; R1 = OEt; R2 = NH2) in aqueous dioxane with HONO gave 5-benzyloxy-2-pyrimidinone and 5-ethoxy-2-pyrimidinone, resp. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Reference of 1753-48-6).

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. 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 1753-48-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts