Tag: 200-300

Base-mediated cascade amidination/N-alkylation of amines by alcohols was written by Zhang, Chunyan;Liang, Zuyu;Lu, Fenghong;Jia, Xiaofei;Zhang, Guoying;Hu, Mao-Lin. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Electric Literature of C14H12N2 This article mentions the following:

A base-mediated cascade amidination/N-alkylation reaction of amines by alcs. was developed. For the first time, nitriles was identified as an efficient and benign water acceptor reagent in N-alkylation. Notably, the procedure tolerates a series of functional groups, such as methoxyl, halo, vinyl and hetero groups, providing a convenient method to construct different substituted diamino compounds, ¹⁵N labeled amine and was scaled up to 1 mol scale offering 138.7 g of the desired product in good yield in one-pot. Mechanistic studies provided strong evidence for the amidination of amines with nitriles facilitated by t-BuOK. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Electric Literature of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. 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.Electric Literature of C14H12N2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Modular Continuous Flow Synthesis of Imatinib and Analogues was written by Fu, Wai Chung;Jamison, Timothy F.. And the article was included in Organic Letters in 2019.Electric Literature of C12H14N2O This article mentions the following:

A modular continuous flow synthesis of imatinib (I) and analogs is reported. Structurally diverse imatinib analogs are rapidly generated using three readily available building blocks via a flow hydration/chemoselective C-N coupling sequence. The newly developed continuous flow hydration and amidation modules each exhibit a broad scope with good to excellent yields. Overall, the method described does not require solvent switches, in-line purifications, or packed-bed apparatuses due to the judicious manipulation of flow setups and solvent mixtures In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Electric Literature of C12H14N2O).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) 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. Electric Literature of C12H14N2O

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Iron-Catalyzed Oxidative Amination of Benzylic C(sp³)-H Bonds with Anilines was written by Song, Yan-Ling;Li, Bei;Xie, Zhen-Biao;Wang, Dan;Sun, Hong-Mei. And the article was included in Journal of Organic Chemistry in 2021.Safety of 4-(Benzylamino)benzonitrile This article mentions the following:

Iron-catalyzed oxidative amination of benzylic C(sp³)-H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) has been realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of the iron metal center. Using DTBP as oxidant, [HItBu][FeBr₄] (1,3-di-tert-butylimidazolium iron tetrabromide) showed the highest catalytic activity for anilines bearing EWGs, while [HIPym][FeBr₄] (1,3-bis(pyrimidin-2-yl)imidazolium iron tetrabromide) was more efficient for EDG-substituted anilines. This work provides an alternative access to benzylamines, e.g., RN(R¹)CH₂Ph [R = 4-O₂NC₆H₄, 2-pyrimidinyl, 8-isoquinolinyl, etc., R¹ = H, Me,], with advantages of both a wide substrate scope and iron catalysis. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Safety of 4-(Benzylamino)benzonitrile).

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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Safety of 4-(Benzylamino)benzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Optimization of N-benzyl-5-nitrofuran-2-carboxamide as an antitubercular agent was written by Gallardo-Macias, Ricardo;Kumar, Pradeep;Jaskowski, Mark;Richmann, Todd;Shrestha, Riju;Russo, Riccardo;Singleton, Eric;Zimmerman, Matthew D.;Ho, Hsin Pin;Dartois, Veronique;Connell, Nancy;Alland, David;Freundlich, Joel S.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Recommanded Product: 37812-51-4 This article mentions the following:

The optimization campaign for a nitrofuran antitubercular hit (N-benzyl-5-nitrofuran-2-carboxamide; JSF-3449) led to the design, synthesis, and biol. profiling of a family of analogs. These compounds exhibited potent in vitro antitubercular activity (MIC = 0.019-0.20 μM) against the Mycobacterium tuberculosis H37Rv strain and low in vitro cytotoxicity (CC₅₀ = 40- > 120 μM) towards Vero cells. Significant improvements in mouse liver microsomal stability and mouse pharmacokinetic profile were realized by introduction of an α,α-dimethylbenzyl moiety. Among these compounds, JSF-4088 (I) is highlighted due to its in vitro antitubercular potency (MIC = 0.019 μM) and Vero cell cytotoxicity (CC₅₀ > 120 μM). The findings suggest a rationale for the continued evolution of this promising series of antitubercular small mols. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Recommanded Product: 37812-51-4).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) 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. 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.Recommanded Product: 37812-51-4

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A facile, choline chloride/urea catalyzed solid phase synthesis of coumarins via Knoevenagel condensation was written by Harishkumar, Hosanagara N.;Mahadevan, Kittappa M.;Kiran Kumar, Hittalumane C.;Satyanarayan, Nayak D.. And the article was included in Organic Communications in 2011.Related Products of 51473-74-6 This article mentions the following:

The influence of choline chloride/urea ionic liquid in solid phase on the Knoevenagel condensation is demonstrated. The active methylene compounds such as meldrum acid, diethylmalonate, Et cyanoacetate, dimethylmalonate, were efficiently condensed with various salicylaldehydes in presence of choline chloride/urea ionic liquid without using any solvents or addnl. catalyst. The reaction is remarkably facile because of the air and water stability of the catalyst, and needs no special precautions. The reactions were completed within 1 h with excellent yields (95%). The products formed were sufficiently pure, and can be easily recovered. The use of ionic liquid choline chloride/urea in solid phase offered several significant advantages such as low cost, greater selectivity and easy isolation of products. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Related Products of 51473-74-6).

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. 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 51473-74-6

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Efficient Access to 2,6,8-Trisubstituted 4-Aminoquinazolines through Microwave-Assisted One-Pot Chemoselective Tris-Suzuki-Miyaura or S_NAr/Bis-Suzuki-Miyaura Reactions in Water was written by Kabri, Youssef;Crozet, Maxime D.;Terme, Thierry;Vanelle, Patrice. And the article was included in European Journal of Organic Chemistry in 2015.Application In Synthesis of 2-Amino-3,5-dibromobenzonitrile This article mentions the following:

An efficient, sequential, one-pot strategy for synthesizing polyfunctionalized quinazoline derivatives is presented. After selective amination of 6,8-dibromo-2,4-dichloroquinazoline at the C-4 position, 2,6,8-trisubstituted 4-aminoquinazoline derivatives I (R = 4-MeOC₆H₄, 4-ClC₆H₄, pyridin-3-yl, etc.) were prepared through one-pot chemoselective sequential tris-Suzuki-Miyaura or S_NAr/bis-Suzuki-Miyaura reactions under microwave irradiation in an aqueous medium. This approach, used with a variety of boronic acids, affords polysubstituted quinazoline derivatives in good to excellent yields in only a few steps and in the environmentally benign solvent water. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Application In Synthesis of 2-Amino-3,5-dibromobenzonitrile).

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

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mononuclear half-sandwich iridium and rhodium complexes through C-H activation: Synthesis, characterization and catalytic activity was written by Yao, Zi-Jian;Li, Kuan;Li, Peng;Deng, Wei. And the article was included in Journal of Organometallic Chemistry in 2017.HPLC of Formula: 10282-32-3 This article mentions the following:

A series of mononuclear half-sandwich cyclometalated group 9 (Ir and Rh) metal complexes were synthesized in good yields through metal-mediated C-H bond activation. These air-stable C, N-chelate mode complexes have similar solid state structures. Both exptl. results and DFT calculations confirmed that no binuclear complexes were generated in this reaction. The iridium complex 3a exhibited good catalytic activity for the reduction of both electron-rich and electron-poor aryl imines with low catalyst loading in the presence of formic acid/triethylamine (F/T) azeotropic mixture All complexes were fully characterized by elemental anal. and IR and NMR spectroscopies. The structures were further confirmed by single-crystal X-ray anal. 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. 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.HPLC of Formula: 10282-32-3

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Excited State Dipole Moments from an Efficient Analysis of Solvatochromic Stokes Shift Data was written by Mosurkal, Ravi;Samanta, A.;Radhakrishnan, T. P.. And the article was included in Journal of Physical Chemistry in 1994.Synthetic Route of C18H10N2 This article mentions the following:

It is shown that the solvatochromism of Stokes shifts has superior correlation with the solvent polarity function E_T^N, and the theor. basis for this is analyzed. The estimation of reliable excited state dipole moments from this correlation as well as the practical advantage of the method in terms of the possibility of employing mixed solvents is demonstrated. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Synthetic Route of C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Synthetic Route of C18H10N2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

CuI/Oxalic Diamide Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amines was written by Zhou, Wei;Fan, Mengyang;Yin, Junli;Jiang, Yongwen;Ma, Dawei. And the article was included in Journal of the American Chemical Society in 2015.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:

A class of oxalic diamides are found to be effective ligands for promoting CuI-catalyzed aryl amination with less reactive (hetero)aryl chlorides. The reaction proceeds at 120 °C with K₃PO₄ as the base in DMSO to afford a wide range of (hetero)aryl amines in good to excellent yields. The bis(N-aryl) substituted oxalamides are superior ligands to N-aryl-N’-alkyl substituted or bis(N-alkyl) substituted oxalamides. Both the electronic nature and the steric property of the aromatic rings in ligands are important for their efficiency. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Quality Control of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. 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.Quality Control of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation was written by Wang, Erfei;Chen, Kaixuan;Chen, Yinan;Zhang, Jiawei;Lin, Xinrong;Chen, Mao. And the article was included in Science China: Chemistry in 2021.Formula: C14H12N2 This article mentions the following:

A porous polymeric ligand (PPL) has been synthesized and complexed with copper to generate a heterogeneous catalyst (Cu@PPL) that has facilitated the efficient C-N coupling with various (hetero)aryl chlorides under mild conditions of visible-light irradiation at 80° (58 examples, up to 99% yields). This method could be applied to both aqueous ammonia and substituted amines, and is compatible to a variety of functional groups and heterocycles, as well as allows tandem C-N couplings with conjunctive dihalides. Furthermore, the heterogeneous characteristic of Cu@PPL has enabled a straightforward catalyst separation in multiple times of recycling with negligible catalytic efficiency loss by simple filtration, affording reaction mixtures containing less than 1 ppm of Cu residue. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Formula: C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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 addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Formula: C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts