Tag: 200-300

Synthesis of new iminocoumarins and their transformations into N-chloro and hydrazono compounds was written by Volmajer, Julija;Toplak, Renata;Leban, Ivan;Majcen Le Marechal, Alenka. And the article was included in Tetrahedron in 2005.Application In Synthesis of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

The Knoevenagel reaction between 2-hydroxybenzaldehydes and active methylene compounds (malononitrile and Et cyanoacetate) produced iminocoumarins, e.g., I, and/or coumarins. In order to study the reactivity of the prepared iminocoumarins, chlorination and reaction with N-nucleophiles were studied. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Application In Synthesis of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and dyeing characteristics of ethyl 1-(2-acetamido-3-cyano-5-carbethoxythiophen-4-yl)glyoxalate(aryl)hydrazones was written by Sabnis, R. W.;Rangnekar, D. W.. And the article was included in Indian Journal of Fibre & Textile Research in 1992.Formula: C12H14N2O4S This article mentions the following:

Five monoazo disperse dyes, Et 1-(2-acetamido-3-cyano-5-carbethoxythiophen-4-yl)glyoxalate-(aryl)hydrazones, were prepared and their dyeing performance on polyester fibers was assessed. The dyeings on polyester had orange red and bright red shades with low pickup, moderate light fastness and good sublimation fastness. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Formula: C12H14N2O4S).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) 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.Formula: C12H14N2O4S

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An Efficient Metal-Free Method for the Denitrosation of Aryl N-Nitrosamines at Room Temperature was written by Chaudhary, Priyanka;Korde, Rishi;Gupta, Surabhi;Sureshbabu, Popuri;Sabiah, Shahulhameed;Kandasamy, Jeyakumar. And the article was included in Advanced Synthesis & Catalysis in 2018.Related Products of 10282-32-3 This article mentions the following:

A simple and practical method for the denitrosation of aryl N-nitrosamines to secondary amines is reported under metal-free conditions using iodine and triethylsilane. Several reduction-susceptible functional groups such as alkene, alkyne, nitrile, nitro, aldehyde, ketone and ester are very stable during the denitrosation, which is remarkable. Broad substrate scope, room temperature reactions and excellent yields are the addnl. features of the current methodol. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Related Products of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. Related Products of 10282-32-3

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of Secondary Amines from One-Pot Reductive Amination with Formic Acid as the Hydrogen Donor over an Acid-Resistant Cobalt Catalyst was written by Jiang, Liang;Zhou, Peng;Zhang, Zehui;Jin, Shiwei;Chi, Quan. And the article was included in Industrial & Engineering Chemistry Research in 2017.Synthetic Route of C14H12N2 This article mentions the following:

Developing new heterogeneous non-noble metal catalysts to replace noble-metal catalysts in organic transformations is of high importance in modern synthetic chem. Herein, nitrogen-doped carbon embedded Co catalysts (abbreviated as Co@CN-T-AT, in which T represents the pyrolysis temperature, AT represents the acid-leaching process) were prepared through the simple pyrolysis of graphene oxide-supported cobalt-based zeolitic imidazolate-frameworks, followed by the acid-leaching process. The Co@CN-600-AT catalyst demonstrated the highest catalytic activity among the synthesized Co catalyst toward the reductive amination of carbonyl compounds with nitro compounds by transfer hydrogenation with formic acid as the hydrogen donor, which integrated three consecutive steps into a one-pot reaction. By applying this catalyst, structurally diverse secondary amines were produced in good to excellent yields without the reduction of other functional groups. The transfer hydrogenation of the imines (C=N bonds) was the rate-determining step. Furthermore, the catalyst was highly stable and could be reused without decrease of the catalytic activity. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Synthetic Route of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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).Synthetic Route of C14H12N2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1,2,4-Triazolo-[1,5-a]pyridine HIF Prolylhydroxylase Domain-1 (PHD-1) Inhibitors With a Novel Monodentate Binding Interaction was written by Ahmed, Saleh;Ayscough, Andrew;Barker, Greg R.;Canning, Hannah E.;Davenport, Richard;Downham, Robert;Harrison, David;Jenkins, Kerry;Kinsella, Natasha;Livermore, David G.;Wright, Susanne;Ivetac, Anthony D.;Skene, Robert;Wilkens, Steven J.;Webster, Natalie A.;Hendrick, Alan G.. And the article was included in Journal of Medicinal Chemistry in 2017.SDS of cas: 1114546-30-3 This article mentions the following:

Herein the authors describe the identification of 4-{[1,2,4]triazolo[1,5-a]pyridin-5-yl}benzonitrile-based inhibitors of the hypoxia-inducible factor prolylhydroxylase domain-1 (PHD-1) enzyme. These inhibitors were shown to possess a novel binding mode by x-ray crystallog., in which the triazolo N1 atom coordinates in a hitherto unreported monodentate interaction with the active site Fe²⁺ ion, while the benzonitrile group accepts a hydrogen-bonding interaction from the side chain residue of Asn 315. Further optimization led to potent PHD-1 inhibitors with good physicochem. and pharmacokinetic properties. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-fluoro-3-methylbenzonitrile (cas: 1114546-30-3SDS of cas: 1114546-30-3).

4-Bromo-2-fluoro-3-methylbenzonitrile (cas: 1114546-30-3) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).SDS of cas: 1114546-30-3

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Palladium-Catalyzed Amination of Aryl Nonaflates was written by Anderson, Kevin W.;Mendez-Perez, Maria;Priego, Julian;Buchwald, Stephen L.. And the article was included in Journal of Organic Chemistry in 2003.HPLC of Formula: 10282-32-3 This article mentions the following:

The first detailed study of the palladium-catalyzed amination of aryl nonaflates is reported. Use of ligands such as BINAP allows for the catalytic amination of electron-rich and -neutral aryl nonaflates with both primary and secondary amines. With use of Xantphos, the catalytic amination of a variety of functionalized aryl nonaflates resulted in excellent yields of anilines; even 2-carboxymethyl aryl nonaflate is effectively coupled with a primary alkylamine. Moderate yields were obtained when coupling halo-aryl nonaflates with a variety of amines, where in most cases the aryl nonaflate reacted in preference to the aryl halide. Overall, aryl nonaflates are an effective alternative to triflates in palladium-catalyzed C-N bond-forming processes due to their increased stability under the reaction conditions. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3HPLC of Formula: 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.HPLC of Formula: 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Studies on the in vitro hepatic microsomal formation of amides during the metabolism of certain secondary and tertiary benzylic amines was written by Ulgen, M.;Gorrod, J. W.. And the article was included in European Journal of Drug Metabolism and Pharmacokinetics in 2000.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

A review with 21 references Part of our interest during the last few years has been to investigate the possible intermediate(s) and mechanism(s) involved in the formation of amides from N-benzylic amines. A number of benzylic amines with different aryl and alkyl moieties introduced onto the constituent nitrogen were prepared, thus creating a wide variety of secondary, tertiary and heterocyclic benzylic amines with different logP and pKa characteristics (Tables I & II). In some experiments, the possible intermediates of this reaction, i.e. nitrones (Table III), imines (Table IV) and amides themselves (Table V), were used as substrates in our metabolic studies. Their in vitro hepatic microsomal metabolism was studied in order to obtain a structure/metabolic activity relationship for the formation of amides from benzylic amines. This communication reviews these studies and reports our conclusions as to the mechanism of formation of amides from N-benzylic amines. 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Name: 4-(Benzylamino)benzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

N-Alkylation of Amines with Alcohols Catalyzed by a Water-Soluble Cp^*Iridium Complex: An Efficient Method for the Synthesis of Amines in Aqueous Media was written by Kawahara, Ryoko;Fujita, Ken-ichi;Yamaguchi, Ryohei. And the article was included in Advanced Synthesis & Catalysis in 2011.Product Details of 10282-32-3 This article mentions the following:

An efficient and environmentally benign catalytic system for the synthesis of various organic amines catalyzed by the water-soluble and air-stable (pentamethylcyclopentadienyl)-iridium-ammine iodide complex, [Cp^*Ir(NH₃)₃][I^–]₂, has been developed. A wide variety of secondary and tertiary amines were synthesized by the N-alkylation reactions of theor. equivalent of amines with alcs. in water under air without a base. The synthesis of cyclic amines was also achieved by the N-alkylation of benzylamine with diols. Furthermore, recycling of the present water-soluble Cp^*Ir catalyst was accomplished. 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 carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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. Product Details of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Metal-free catalysis of the reductive amination of aldehydes using a phosphonium-doped porous aromatic framework was written by You, Bingxin;Zou, Min;Xu, Ruitong;Tian, Yuyang;Wang, Baolin;Zhu, Guangshan. And the article was included in Molecular Catalysis in 2022.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

In this study, OTf@PAF-180, a porous aromatic framework (PAF) containing rich Lewis acidic phosphonium centers and triflate (-OTf) counter anions, was prepared via Yamamoto-type Ullmann cross-coupling of tris(4-bromophenyl)phosphane and subsequent treatment with Me triflate (MeOTf). It showed high performance in catalyzing the reductive amination of aldehydes using dimethylphenylsilane (PhMe₂SiH) as the hydride source, and a variety of amines were prepared in this way with good to excellent yields. As a metal-free heterogeneous catalyst, OTf@PAF-180 also exhibited excellent recyclability and retained high catalytic activity after five consecutive cycles. The high activity, recyclability and stability of OTf@PAF-180 made it a promising novel heterogeneous catalyst for organic synthesis. 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. 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: 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Convenient synthesis of disubstituted tacrine derivatives via electrophilic and copper induced reactions was written by Ekiz, Makbule;Tutar, Ahmet;Okten, Salih. And the article was included in Tetrahedron in 2016.Application of 68385-95-5 This article mentions the following:

The bromination of 2-aminobenzonitrile with mol. bromine (2 equiv) furnished 2-amino-3,5-dibromobenzonitrile in 98% yield. One-pot syntheses are described for dibromotacrine derivatives, e.g., I (Y = CH₂), utilizing Friedlander reactions. A convenient route is described for disubstituted derivatives of tacrines from dibromotacrine I (Y = CH₂, CH₂CH₂) (II) by various substitution reactions. Several disubstituted tacrines were synthesized by treatment of II with n-BuLi followed by trapping with an electrophile [Si(Me)₃Cl, S₂(Me)₂]. Both were converted to the corresponding cyano derivatives III (X = Br, Y = CH₂; X = CN, Y = CH₂; X = CN, CH₂CH₂) via copper-assisted nucleophilic substitution reactions in moderate yields (30%, 50%, and 60%, resp.). Copper-induced nucleophilic substitution of dibromide II (Y = CH₂CH₂) with NaOMe afforded mono-methoxide IV in 25% yield. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Application of 68385-95-5).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. 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.Application of 68385-95-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts