Nitriles-buliding-blocks

Regioselective Hydration of Terminal Alkynes Catalyzed by a Neutral Gold(I) Complex [(IPr)AuCl] and One-Pot Synthesis of Optically Active Secondary Alcohols from Terminal Alkynes by the Combination of [(IPr)AuCl] and Cp*RhCl[(R,R)-TsDPEN] was written by Li, Feng;Wang, Nana;Lu, Lei;Zhu, Guangjun. And the article was included in Journal of Organic Chemistry in 2015.SDS of cas: 101219-69-6 This article mentions the following:

A neutral gold(I) complex [(IPr)AuCl] [IPr = 1,3-bis(diisopropylphenyl)imidazol-2-ylidene] was found to be a highly effective catalyst for the hydration of terminal alkynes, including aromatic alkynes and aliphatic alkynes. The desired Me ketones were obtained in high yields with complete regioselectivities. Furthermore, a series of optically active secondary alcs. could be obtained in high yield with good to excellent enantioselectivities via one-pot sequential hydration/asym. transfer hydrogenation (ATH) from terminal alkynes by the combination of of [(IPr)AuCl] and Cp*RhCl[(R,R)-TsDPEN] [Cp* = pentamethylcyclopentadienyl, TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]. Notably, this research exhibited the potential of the direct use of neutral gold(I) complexes instead of cationic ones as catalysts for the activation of multiple bonds for organic synthesis. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6SDS of cas: 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. 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.SDS of cas: 101219-69-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ethyl 2-(3-phenylthioureido)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate was written by de Oliveira, Jaismary G. B.;Mendonca, Francisco J. B. Jr.;de Lima, Maria do Carmo A.;de Simone, Carlos A.;Ellena, Javier A.. And the article was included in Acta Crystallographica, Section E: Structure Reports Online in 2012.Reference of 70291-62-2 This article mentions the following:

In the title compound, C₁₇H₁₈N₂O₂S₂, the angle between the mean plane defined by the atoms of the 5,6-dihydro-4H-cyclopenta[b]thiophene moiety (root-mean-square deviation = 0.19 鑴? and the Ph ring is 72.8鎺?2). The mol. conformation is stabilized by an intramol. N-H璺矾璺疧 interaction, which generates an S(6) ring motif. In the crystal, pairs of N-H璺矾璺疭 H bonds link the mols. to form inversion dimers with an R₂²(8) ring motif. Crystallog. data and at. coordinates are given. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Reference of 70291-62-2).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An efficient method for the selective iridium-catalyzed monoalkylation of (hetero)aromatic amines with primary alcohols was written by Blank, Benoit;Madalska, Martyna;Kempe, Rhett. And the article was included in Advanced Synthesis & Catalysis in 2008.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

An efficient multi-gram scale synthesis protocol of a variety of P,N ligands is described. The synthesis is achieved in a two-step reaction. First, the amine is deprotonated and subsequently the chlorophosphine is added to yield the corresponding P,N ligand. Deprotonation of the amine is normally achieved with BuLi at low temperature, but for the preparation of ligands with a 2,2′-dipyridylamino backbone and phosphines with a high steric demand KH has to be employed in combination with reaction temperatures of 110鎺矯 for the salt metathesis step. The reaction of two equivalent of a selected P,N ligand with one equivalent of the iridium complex [IrCl(cod)]₂ (cod = 1,5-cyclooctadiene) affords P,N ligand-coordinated iridium complexes in quant. yield. X-Ray single crystal structure anal. of one of these complexes reveals a monomeric five-coordinated structure in the solid state. The iridium complexes were used to form catalysts for the N-alkylation of aromatic amines with alcs. The catalyst system was optimized by studying 8 different P,N ligands, 9 different solvents and 14 different bases. Systematic variation of the substrate to base and the amine to alc. ratios as well as the catalyst loading led to optimized catalytic reaction conditions. The substrate scope of the developed catalytic protocol was shown by synthesizing 20 different amines of which 12 could be obtained in isolated yields higher than 90%. A new efficient catalyst system for the selective monoalkylation of primary aromatic and heteroaromatic amines with primary aromatic, heteroaromatic as well as aliphatic alcs. has been established. The reaction proceeds with rather moderate catalyst loadings. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Name: 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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.Name: 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Facile pathway for synthesis of two efficient catalysts for preparation of 2-aminothiophenes and tetrahydrobenzo[b]pyrans was written by Saadati-Moshtaghin, Hamid Reza;Zonoz, Farrokhzad Mohammadi. And the article was included in Research on Chemical Intermediates in 2018.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Abstract: We report here a new magnetically recyclable catalyst consisting of iron-substituted Keggin-type heteropolyacid (HPA) grafted on modified Fe₃O₄ nanoparticles. The synthesized hybrid nanomaterial exhibited the excellent catalytic efficiency in condensation reaction for the preparation of tetrahydrobenzo[b]pyrans under solvent-free conditions as well as in the synthesis of 2-aminothiophenes via Gewald reaction. It must be noted that, HPA supported magnetite nanoparticles catalyzed the preparation of tetrahydrobenzo[b]pyrans, whereas for Gewald reaction amine-functionalized magnetite nanoparticles acted as a catalyst. Different characterization techniques such as Fourier transform IR (FT-IR), X-ray powder diffraction (XRD), field emission SEM (FESEM), transmission electron microscopy (TEM) and vibrating sample magnetometer (VSM) were used to characterize the hybrid nanomaterial. The reusability of catalyst was affirmed by using in consecutive runs for five times. Performance of prepared catalyst was compared with the various previously reported catalysts; the newly synthesized catalysts found to be most efficient with regard to reaction time, yield and ease of catalyst separation In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 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. 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.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via Isocyanide Insertion was written by Wang, Xu;Xiong, Wenfang;Huang, Yubing;Zhu, Jiayi;Hu, Qiong;Wu, Wanqing;Jiang, Huanfeng. And the article was included in Organic Letters in 2017.Recommanded Product: 2-(2,6-Dibromophenyl)acetonitrile This article mentions the following:

A new and versatile multicomponent domino strategy has been developed for the synthesis of a series of 1H-indene and phthalimide derivatives from simple and readily available starting materials. This process operating under mild conditions shows a broad substrate scope with moderate to excellent yields. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9Recommanded Product: 2-(2,6-Dibromophenyl)acetonitrile).

2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C閳ユ弲 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.Recommanded Product: 2-(2,6-Dibromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The novel reaction of ketones with o-oxazoline-substituted anilines was written by Luo, Fen-Tair;Ravi, Vija K.;Xue, Cuihua. And the article was included in Tetrahedron in 2006.Synthetic Route of C7H5ClN2 This article mentions the following:

A variety of ketones reacted with o-oxazoline-substituted anilines in the presence of catalytic amount of p-toluenesulfonic acid in dry n-butanol to form 4-amino-substituted quinolines or 4-quinolones in fair to good yields. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Synthetic Route of C7H5ClN2).

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. 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. Synthetic Route of C7H5ClN2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Tungsten-Catalyzed Direct N-Alkylation of Anilines with Alcohols was written by Lan, Xiao-Bing;Ye, Zongren;Yang, Chenhui;Li, Weikang;Liu, Jiahao;Huang, Ming;Liu, Yan;Ke, Zhuofeng. And the article was included in ChemSusChem in 2021.Product Details of 10282-32-3 This article mentions the following:

A tungsten-catalyzed N-alkylation reaction of anilines with primary alcs. via BH/HA (Borrowing Hydrogen/Hydrogen Autotransfer) were reported. This phosphine-free W(phen)(CO)₄ (phen = 1,10-phenthroline) system was demonstrated as a practical and easily accessible in-situ catalysis for a broad range of amines and alcs. (up to 49 examples, including 16 previously undisclosed products). Notably, this tungsten system tolerated numerous functional groups, especially the challenging substrates with sterically hindered substituents or heteroatoms. Mechanistic insights based on exptl. and computational studies were provided. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Product Details of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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 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.Product Details of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Efficient cyanation of aryl bromides with K₄[Fe(CN)₆] catalyzed by a palladium-indolylphosphine complex was written by Yeung, Pui Yee;Tsang, Chun Pui;Kwong, Fuk Yee. And the article was included in Tetrahedron Letters in 2011.Formula: C8H8N2 This article mentions the following:

This study describes a general palladium-catalyzed cyanation of aryl bromides using K₄[Fe(CN)₆] as the cyanide surrogate. The reactions can be successfully conducted under mild reaction conditions (at 50鎺矯) in mixed solvents (water/MeCN = 1:1) without any surfactant additives, and afford the desired aryl nitriles in good-to-excellent yields. Particularly noteworthy is that this system allows the mildest reaction temperature reported so far for palladium-catalyzed cyanation of aryl bromides with K₄[Fe(CN)₆] source in general. Common functional groups, including keto, aldehyde, free amine, and heterocyclic substrates are compatible under this system. Interestingly, the phosphine ligands bearing -PCy₂ moiety, which usually show excellent activity in aryl halide couplings, are found less effective than the corresponding ligands with -PPh₂ group. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Formula: C8H8N2).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. Formula: C8H8N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Light-mediated cyanomethylation of cycloalkenes with acetonitrile was written by Sonawane, Harikisan R.;Bellur, Nanjundiah S.;Shah, Virendra G.. And the article was included in Journal of the Chemical Society, Chemical Communications in 1990.SDS of cas: 4435-14-7 This article mentions the following:

The addition of cyanomethyl radicals, generated from MeCN via photoinduced decomposition of H₂O₂, to cycloalkenes gave cycloalkylmethyl nitriles and cycloalkanols. The homolytic cyanomethylation of 3,3-dimethyl-2-methylenebicyclo[2.2.1]heptane gave endo-2-(2-cyanoethyl)- and endo-2-(hydroxymethyl)-3,3-dimethylbicyclo[2.2.1]heptane in 76% overall yield in a 49:51 product ratio. The homolytic cyanomethylation of norbornene gave exo-2-(cyanomethyl)bicyclo[2.2.1]heptane and exo-norborneol in 72% overall yield in a 80:20 product ratio. The reaction mechanism was discussed. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7SDS of cas: 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閳ユ弲 bond formation or by dehydration of primary carboxamides. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).SDS of cas: 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts