Month: October 2022

In 2022,Huang, Weichen; Keess, Sebastian; Molander, Gary A. published an article in Journal of the American Chemical Society. The title of the article was 《Dicarbofunctionalization of [1.1.1]Propellane Enabled by Nickel/Photoredox Dual Catalysis: One-Step Multicomponent Strategy for the Synthesis of BCP-Aryl Derivatives》.Reference of 2-Bromobenzonitrile The author mentioned the following in the article:

Bicyclo[1.1.1]pentane (BCP) motifs as para-disubstituted aryl bioisosteres are playing an emerging role in pharmaceutical, agrochem., and materials chem. The vast majority of these structures are obtained from a BCP electrophile or nucleophile, which are themselves derived from [1.1.1]propellane via cleavage of the internal C-C bond through the addition of either radicals or metal-based nucleophiles. Compared with the current stepwise approaches, a multicomponent reaction that provides direct access to complex and diverse disubstituted BCP products would be more attractive. Herein, authors report a single-step, multicomponent approach to synthetically versatile arylated BCP products via nickel/photoredox catalysis. Importantly, this three-component process allows two C-C bonds to be formed in a single step and sets three quaternary centers, unprecedented in any previously reported methods. The method has been demonstrated to allow access to complex BCP architectures from aryl halide and radical precursor substrates. In the experimental materials used by the author, we found 2-Bromobenzonitrile(cas: 2042-37-7Reference of 2-Bromobenzonitrile)

2-Bromobenzonitrile(cas: 2042-37-7) is a precursor to the quinazolinones, a class of drugs used to treat autoimmune diseases and coronary heart disease. This substrate molecule undergoes a palladium-catalyzed coupling reaction to form an aromatic ring. The light emission from this reaction can be seen in the reaction solution.Reference of 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 3-Oxo-3-phenylpropanenitrileIn 2022 ,《Synthesis and in vitro antiproliferative activity of certain novel pyrazolo[3,4-b]pyridines with potential p38α MAPK-inhibitory activity》 appeared in Archiv der Pharmazie (Weinheim, Germany). The author of the article were Farahat, Aya A.; Samir, Eman M.; Zaki, Mayssoune Y.; Serya, Rabah A. T.; Abdel-Aziz, Hatem A.. The article conveys some information:

Novel series of pyrazolo[3,4-b]pyridines 9a-j and 14a-f were prepared via a one-pot three-component reaction. Compounds 9a-j were synthesized by the reaction of 3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-amine (4) with benzoyl acetonitriles 3a,b and aldehydes 5a-e, whereas the spiro derivatives 14a-f were synthesized by the reaction of pyrazole derivative 4 with 3a-c and indoline-2,3-diones 10a,b. Screening of the antiproliferative activity of 9a-j and 14a-f revealed that 14a and 14d were the most potent analogs against HepG2 and HeLa cells, with IC50 = 4.2 and 5.9 μM, resp. Moreover, compounds 9c and 14a could promote cell cycle disturbance and apoptosis in HepG2 cells, as evidenced by DNA flow cytometry and Annexin V-FITC/PI assays. Cell cycle anal. of 9c and 14a indicated a reduction in HepG2 cells in the G1 phase, with arrest in the S phase and the G2/M phase, resp. Also, 9c and 14a are good apoptotic inducers in the HepG2 cell line. Furthermore, compounds 9h and 14d stood out as the most efficient antiproliferative agents in the NCI 60-cell line panel screening, with mean GI % equal to 60.3% and 55.4%, resp. Addnl., 9c, 9h, 14a, and 14d showed good inhibitory action against the cellular pathway regulator p38α kinase, with IC50 = 0.42, 0.41, 0.13, and 0.64 μM, resp. A docking study was carried out on the p38α kinase active site, showing a binding mode comparable to that of reported p38 mitogen-activated protein kinase inhibitors. These newly discovered pyrazolo[3,4-b]pyridines could be considered as potential candidates for the development of newly targeted anticancer agents. In the experiment, the researchers used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Reference of 3-Oxo-3-phenylpropanenitrile)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used in the synthesis of substituted naphtho[1,8-bc]pyrans. It was also used as building block in the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics.Reference of 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

COA of Formula: C7H3BrFNIn 2019 ,《Discovery of novel pan-genotypic HCV NS5A inhibitors containing a novel tetracyclic core》 was published in Bioorganic & Medicinal Chemistry Letters. The article was written by Yu, Wensheng; Hu, Bin; Zhong, Bin; Hao, Jinglai; Lei, Zhixin; Agrawal, Sony; Rokosz, Laura; Liu, Rong; Chen, Shiying; Asante-Appiah, Ernest; Kozlowski, Joseph A.. The article contains the following contents:

A series of novel tetracyclic core-containing HCV NS5A inhibitors has been discovered. Incorporation of tetrahydropyran-substituted amino acid moiety improved their potency and yielded HCV NS5A inhibitors with a min. potency shift from the GT1a strain compared to other genotypes and mutants. Compounds 53 and 54 showed the best potency profile and had reasonable half-times in rat PK studies. However, further optimization of their oral bioavailability is still needed in order to advance them for further development. [BMCL Abstract] 2000 Elsevier Science Ltd. All rights reserved. In addition to this study using 4-Bromo-2-fluorobenzonitrile, there are many other studies that have used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3COA of Formula: C7H3BrFN) was used in this study.

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.COA of Formula: C7H3BrFN It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ali, Abdelselam; Bliese, Marianne; Rasmussen, Jo-Anne M.; Sargent, Roger M.; Saubern, Simon; Sawutz, David G.; Wilkie, John S.; Winkler, David A.; Winzenberg, Kevin N.; Woodgate, Ruth C. J. published an article on February 15 ,2007. The article was titled 《Discovery of (Z)-2-phenyl-3-(1H-pyrrol-2-yl)acrylonitrile derivatives active against Haemonchus contortus and Ctenocephalides felis (cat flea)》, and you may find the article in Bioorganic & Medicinal Chemistry Letters.Application In Synthesis of 3-Chloro-4-fluorophenylacetonitrile The information in the text is summarized as follows:

A series of 2-phenyl-3-(1H-pyrrol-2-yl)acrylonitrile derivatives, e.g., I, were synthesized and evaluated for in vitro activity against the endoparasite Haemonchus contortus and the ectoparasite Ctenocephalides felis. Some compounds had significant in vitro activity against these parasites. The experimental process involved the reaction of 3-Chloro-4-fluorophenylacetonitrile(cas: 658-98-0Application In Synthesis of 3-Chloro-4-fluorophenylacetonitrile)

3-Chloro-4-fluorophenylacetonitrile(cas: 658-98-0) belongs to nitriles. Nitriles are found in many useful compounds. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.Application In Synthesis of 3-Chloro-4-fluorophenylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liras, Spiros; Lynch, Christopher L.; Fryer, Andrew M.; Vu, Binh T.; Martin, Stephen F. published an article in Journal of the American Chemical Society. The title of the article was 《Applications of Vinylogous Mannich Reactions. Total Syntheses of the Ergot Alkaloids Rugulovasines A and B and Setoclavine》.Application of 89245-35-2 The author mentioned the following in the article:

Concise syntheses of the Ergot alkaloids rugulovasine A [I; R1 = H, R2 = β-H, R3 = Me, (II)], rugulovasine B I [R1 = H, R2 = α-H, R3 = Me (III)], and setoclavine (IV) have been completed by strategies that feature inter- and intramol. vinylogous Mannich reactions as the key steps. Thus, the first synthesis of II,III commenced with the conversion of the known 4-bromoindole-3-acetonitrile into V via the addition of the 2-(tert-butyldimethylsilyloxy)-3-methylfuran to the iminium ion [VI; CH=N+(Me)Bn], which was generated in situ from the aldehyde VI (R = CHO). Cyclization of V by a novel SRN1 reaction followed by removal of the N-benzyl group furnished a mixture (1:2) of II and III. In an alternative approach to these alkaloids, the biaryl [VII; R = Boc] was reduced with DIBAL-H to give an intermediate imine that underwent spontaneous cyclization via an intramol. vinylogous Mannich addition to provide I [R1 = Boc, R2 = R3 = H]. N-Methylation of the derived benzyl carbamates I [R1 = Boc, R2 = H, R3 = Cbz] followed by global deprotection gave a mixture (2:1) of II and III. IV was then prepared from the biaryl VII (R = Ts) using a closely related intramol. vinylogous Mannich reaction to furnish the spirocyclic lactones I [R1 = Ts, R2 = R3 = H (VIII)]. VIII were subsequently transformed by hydride reduction and reductive methylation into the ergoline derivatives [IX; R = α-OH, β-OH] which were in turn converted into IV by deprotection and solvolytic 1,3-rearrangement of the allylic hydroxyl group. In the experimental materials used by the author, we found 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Application of 89245-35-2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Application of 89245-35-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2008,Jautze, Sascha; Peters, Rene published 《Enantioselective bimetallic catalysis of Michael additions forming quaternary stereocenters》.Angewandte Chemie, International Edition published the findings.Product Details of 31938-07-5 The information in the text is summarized as follows:

Low catalyst loadings of a planar-chiral ferrocenyl bispalladacycle are sufficient to catalyze the Michael addition of trisubstituted α-cyanoacetates to enones with excellent yields (TONs up to 2450) and high enantioselectivity. The reaction proceeds by a cooperative bimetallic mechanism and is superior to previous methods relying on soft Lewis acid catalysts.2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 31938-07-5) was used in this study.

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Product Details of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2013,Vogt, Matthias; Nerush, Alexander; Iron, Mark A.; Leitus, Gregory; Diskin-Posner, Yael; Shimon, Linda J. W.; Ben-David, Yehoshoa; Milstein, David published 《Activation of Nitriles by Metal Ligand Cooperation. Reversible Formation of Ketimido- and Enamido-Rhenium PNP Pincer Complexes and Relevance to Catalytic Design》.Journal of the American Chemical Society published the findings.Reference of 2-(3-Bromophenyl)acetonitrile The information in the text is summarized as follows:

The dearomatized complex cis-[Re-(PNPtBu*)-(CO)2] (4) undergoes cooperative activation of CN triple bonds of nitriles via [1,3]-addition Reversible C-C and Re-N bond formation in 4 was investigated in a combined exptl. and computational study. The reversible formation of the ketimido complexes (5-7) was observed When nitriles bearing an alpha methylene group are used, reversible formation of the enamido complexes (8 and 9) takes place. The reversibility of the activation of the nitriles in the resulting ketimido compounds was demonstrated by the displacement of p-CF3-benzonitrile from cis-[Re-(PNPtBu-N=CPhpCF3)-(CO)2] (6) upon addition of an excess of benzonitrile and by the temperature-dependent [1,3]-addition of pivalonitrile to complex 4. The reversible binding of the nitrile in the enamido compound cis-[Re-(PNPtBu-HNC=CHPh)-(CO)2] (9) was demonstrated via the displacement of benzyl cyanide from 9 by CO. Computational studies suggest a stepwise activation of the nitriles by 4, with remarkably low activation barriers, involving precoordination of the nitrile group to the Re-(I) center. The enamido complex 9 reacts via β-carbon methylation to give the primary imino complex cis-[Re-(PNPtBu-HN=CC-(Me)-Ph)-(CO)2]-OTf 11. Upon deprotonation of 11 and subsequent addition of benzyl cyanide, complex 9 is regenerated and the monomethylation product 2-phenylpropanenitrile is released. Complexes 4 and 9 were found to catalyze the Michael addition of benzyl cyanide derivatives to α,β-unsaturated esters and carbonyls. In addition to this study using 2-(3-Bromophenyl)acetonitrile, there are many other studies that have used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Reference of 2-(3-Bromophenyl)acetonitrile) was used in this study.

According to other reports, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) is used in the preparation of diarylpyrimidines (DAPYs) as HIV-1 non-nucleoside reverse transcriptase inhibitors.Reference of 2-(3-Bromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Welin, Eric R.; Le, Chip; Arias-Rotondo, Daniela M.; McCusker, James K.; MacMillan, David W. C. published 《Photosensitized, energy transfer-mediated organometallic catalysis through electronically excited nickel(II)》.Science (Washington, DC, United States) published the findings.Category: nitriles-buliding-blocks The information in the text is summarized as follows:

Transition metal catalysis has traditionally relied on organometallic complexes that can cycle through a series of ground-state oxidation levels to achieve a series of discrete yet fundamental fragment-coupling steps. The viability of excited-state organometallic catalysis via direct photoexcitation has been demonstrated. Although the utility of triplet sensitization by energy transfer has long been known as a powerful activation mode in organic photochem., it is surprising to recognize that photosensitization mechanisms to access excited-state organometallic catalysts have lagged far behind. Here, we demonstrate excited-state organometallic catalysis via such an activation pathway: Energy transfer from an iridium sensitizer produces an excited-state nickel complex that couples aryl halides with carboxylic acids. Detailed mechanistic studies confirm the role of photosensitization via energy transfer. In the part of experimental materials, we found many familiar compounds, such as 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Category: nitriles-buliding-blocks)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Category: nitriles-buliding-blocks It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Organic Process Research & Development included an article by Perkins, Robert J.; Hughes, Alexander J.; Weix, Daniel J.; Hansen, Eric C.. Reference of 4-Bromobenzonitrile. The article was titled 《Metal-Reductant-Free Electrochemical Nickel-Catalyzed Couplings of Aryl and Alkyl Bromides in Acetonitrile》. The information in the text is summarized as follows:

While reductive cross-electrochem. coupling is an attractive approach for the synthesis of complex mols. at both small and large scale, two barriers for large-scale applications have remained: the use of stoichiometric metal reductants and a need for amide solvents. In this communication, new conditions that address these challenges are reported. The nickel-catalyzed reductive cross-coupling of aryl bromides with alkyl bromides can be conducted in a divided electrochem. cell using acetonitrile as the solvent and diisopropylamine as the sacrificial reductant to afford coupling products in synthetically useful yields (22-80%). Addnl., the use of a combination of the ligands 4,4′,4”-tri-tert-butyl-2,2′:6′,2′-terpyridine and 4,4′-di-tert-butyl-2,2′-bipyridine is essential to achieve high yields. In the experiment, the researchers used many compounds, for example, 4-Bromobenzonitrile(cas: 623-00-7Reference of 4-Bromobenzonitrile)

4-Bromobenzonitrile(cas: 623-00-7) is classified as organic nitriles, which are commonly use solvents and are reacted further for various applications such as manufacture of polymers and intermediates for pharmaceuticals and other organic chemicals,Reference of 4-Bromobenzonitrile It can also be used as an aryl halide test compound in developing greener reaction conditions for Suzuki cross-coupling between aryl halides and phenyl boronic acid.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Lan, Chunling Blue; Auclair, Karine published their research in European Journal of Organic Chemistry in 2021. The article was titled 《Ammonium Chloride-Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation》.Application of 1194-02-1 The article contains the following contents:

Ammonium chloride promoted the reaction between amines and potassium cyanate to generate monosubstituted ureas in water. This method proceeded rapidly under microwave irradiation and tolerates a broad range of functional groups. Unlike previous strategies, it was compatible with other nucleophiles, acid-labile moieties and most of the common protecting groups. The products precipitate out of solution, allowing facile isolation without column chromatog. In addition to this study using 4-Fluorobenzonitrile, there are many other studies that have used 4-Fluorobenzonitrile(cas: 1194-02-1Application of 1194-02-1) was used in this study.

4-Fluorobenzonitrile(cas: 1194-02-1) is used in the synthesis of flurenones, pharmaceutical prerequisites, as well as opiod receptor antagonists.Application of 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts