Tag: 100-200

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

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

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

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

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

Identification of novel inhibitors of Aurora A with a 3-(pyrrolopyridin-2-yl)indazole scaffold was written by Song, Pinrao;Chen, Ming;Ma, Xiaodong;Xu, Lei;Liu, Tao;Zhou, Yubo;Hu, Yongzhou. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Recommanded Product: 3-Amino-4-methylbenzonitrile This article mentions the following:

A novel series of 3-(pyrrolopyridin-2-yl)indazole derivatives were synthesized and biol. evaluated for their anti-proliferative effects on five human cancer cell lines. As a result, all of them exhibited vigorous potency against HL60 cell line with IC₅₀ values ranging from singe digital nanomolar to micromolar level. Besides, a majority of them displayed modest to good antiproliferative activities against the other four cell lines, including KB, SMMC-7721, HCT116, and A549. Particularly, compound 2y, as the most distinguished one in this series, demonstrated IC₅₀ values of 8.3 nM and 1.3 nM against HL60 and HCT116 cell lines, resp. Afterwards, for exploring the mol. target, compounds2d, 2g and 2y were further selected to evaluate the inhibitory activities against a panel of kinases. Finally, they were identified to be targeting Aurora A kinase with significant selectivity over other kinases, such as CHK1, CDK2, MEK1, GSK3灏? BRAF, IKK灏?and PKC. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Recommanded Product: 3-Amino-4-methylbenzonitrile).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) belongs to nitriles. The R-C-N bond angle in and nitrile is 180鎺?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 锜? 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.Recommanded Product: 3-Amino-4-methylbenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

2-(Benzoylimino)thiazolidin-4-ones: formation by an alternative ring closure and analysis of rotational barriers was written by Haecker, Hans-Georg;Elsinghorst, Paul W.;Michels, Susanne;Daniels, Joerg;Schnakenburg, Gregor;Guetschow, Michael. And the article was included in Synthesis in 2009.Category: nitriles-buliding-blocks This article mentions the following:

The reactions of N-benzoyl-N’-(o-cyanoaryl)thioureas with Et bromoacetate under alk. conditions led to the formation of either fused 2-(alkylsulfanyl)-4-aminopyrimidines or 2-(benzoylimino)-3-(o-cyanoaryl)thiazolidin-4-ones. The accurate application of slightly different reaction conditions allowed us to adjust the balance between the formation of the pyrimidine or thiazolidine heterocycles. Atropisomerism in the 3-(o-cyanoaryl)thiazolidin-4-ones was influenced by the size of the o-cyanoaryl ring, which was investigated by means of NMR measurements and theor. calculations In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Category: nitriles-buliding-blocks).

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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cone angle of ligands – Group IV and V compounds was written by Imyanitov, N. S.. And the article was included in Koordinatsionnaya Khimiya in 1985.Category: nitriles-buliding-blocks This article mentions the following:

The cone angle (the steric characteristic, expressing the degree of filling out by the ligand of the coordination sphere) was calculated for 610 ligands. The ligands considered have the formulas AX₃ or A(OX)₃ and have tetrahedral geometry with respect to A in the fragment of the complex M-AX₃ (M = coordinating metal; A = N, P, As, Sb, Bi, C, Si, Ge, Sn, Pb; X = alkyl, cycloalkyl, aryl, alkylaryl, arylalkyl). Known cone angles of ligands based on P, determined by mol. models, are correlated; the effective covalent and van der Waals radii of X were calculated with respect to the known cone angles. The cone angles are calculated with respect to the radii and the internuclear M-A distances. This procedure ensures standardization and comparability of the steric characteristics obtained. Cone angles are equal or nearly equal for neighboring elements of group IVA and VA. As the at. number of A in a group increases the cone angle decreases. The change in cone angle was considered in relation to the M-ligand; the cone angle values, established for Ni complexes, can be used for complexes of all other transition metals, except those in the beginning of the transition series. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Category: nitriles-buliding-blocks).

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. 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3H-Azepines and related systems. Part 5. Photo-induced ring expansions of o-azidobenzonitriles to 3-cyano- and 7-cyano-3H-azepin-2(1H)-ones was written by Lamara, Kaddour;Redhouse, Alan D.;Smalley, Robert K.;Thompson, J. Robin. And the article was included in Tetrahedron in 1994.HPLC of Formula: 64113-86-6 This article mentions the following:

Unlike other aryl azides bearing electron-withdrawing ortho-substituents, o-azidobenzonitriles on photolysis in aqueous-tetrahydrofuran yield mixtures of the expected 3-cyano- (I; R=CN, R¹ = R² = H) and the unexpected 7-cyano-3H-azepin-2(1H)-ones (I; R = R¹ = H, R² = CN). In one instance ring-contraction to 2-azabicyclo[3.2.0]hept-6-en-3-one II is noted. X-Ray crystallog. data for 7-cyano- (I; R = R¹ = H, R² = CN) and 4-chloro-7-cyano-3H-azepin-2-one (R = H, R¹ = Cl, R² = CN) , and for the azabicycloheptenone, are presented. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6HPLC of Formula: 64113-86-6).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. The R-C-N bond angle in and nitrile is 180鎺?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 锜? 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: 64113-86-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts