Category: nitriles-buliding-blocks

Stepannikova, Kateryna O.; Vashchenko, Bohdan V.; Grygorenko, Oleksandr O.; Gorichko, Marian V.; Cherepakha, Artem Yu.; Moroz, Yurii S.; Volovenko, Yulian M.; Zhersh, Serhii published their research in European Journal of Organic Chemistry on December 21 ,2021. The article was titled 《Synthesis of Spirocyclic β- and γ-Sultams by One-Pot Reductive Cyclization of Cyanoalkylsulfonyl Fluorides》.Computed Properties of C9H13NO2 The article contains the following contents:

One-pot intramol. cyclization of novel sp3-enriched cyanoalkylsulfonyl fluorides into spirocyclic β- or γ-sultams is disclosed. The method relies on nitrile group reduction followed by sulfonylation of amino group thus formed upon mild conditions (NaBH4, NiCl2·6H2O in MeOH). Cyclization proceeds smoothly with considerable efficiency (48-84%, 10 examples) on up to 30 g scale. The cyanoalkylsulfonyl fluoride intermediates can be obtained via S-nucleophilic substitution in β-functionalized alkanenitriles or double alkylation of α-alkylthioacetonitrile, followed by oxidative chlorination with Cl2 and further reaction with KHF2. The title mono- and bifunctional sultams are advanced sp3-enriched building blocks for drug discovery and organic synthesis providing novel substitution patterns and frameworks mimicking saturated nitrogen heterocycles such as pyrrolidine/pyrrolidone. In the experiment, the researchers used Ethyl 1-cyanocyclopentane-1-carboxylate(cas: 28247-14-5Computed Properties of C9H13NO2)

Ethyl 1-cyanocyclopentane-1-carboxylate(cas: 28247-14-5) is a member of cyclopentanes. Although cyclopentane itself doesn’t have a single highly favoured conformation, a substituent on the cyclopentane ring can upset the balance of strains thereby favouring either the envelope or the half-chair.Computed Properties of C9H13NO2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Design, synthesis, biological evaluation and molecular docking of new uracil analogs-1,2,4-oxadiazole hybrids as potential anticancer agents》 was written by El Mansouri, Az-Eddine; Oubella, Ali; Maatallah, Mohamed; AitItto, Moulay Youssef; Zahouily, Mohamed; Morjani, Hamid; Lazrek, Hassan B.. Recommanded Product: 4-Cyanobenzyl bromideThis research focused onuracil oxadiazole hybrid preparation caspase mol docking anticancer agent; 1,2,4-Oxadiazole; Anticancer activity; Apoptosis; Heterogeneous catalyst; Hybrid molecules; Molecular docking; Uracil analogues. The article conveys some information:

A new series of uracil analogs-1,2,4-oxadiazole hybrid derivatives were synthesized by a new, simple, and efficient method using for the first time HAP-SO3H as an heterogeneous acid catalyst for the condensation and cyclization between amidoxime and aldehyde. The new derivatives were characterized by HRMS, FTIR, 1H NMR, and 13C NMR spectroscopy techniques. The synthesized 1,2,4-oxadiazole hybrids were evaluated for their cytotoxic activity in five human cancer cell lines: melanoma (A-375), fibrosarcoma (HT-1080), breast (MCF-7 and MDA-MB-231), and lung carcinoma (A-549). Compounds 1-[4-(5-Biphenyl-4-yl-[1,2,4]oxadiazol-3-yl)-benzyl]-5-fluoro-1H-pyrimidine-2,4-dione and 5-Fluoro-1-{4-[5-(4′-methoxy-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-1H-pyrimidine-2,4-dione were potent cytotoxic agents against HT-1080 and MFC-7 cells with IC50 inferior to 1μM. The possible mechanism of apoptosis induction by the derivatives was studied using Annexin v staining, caspase-3/7 activity, mitochondrial membrane potential measurement, and anal. cell cycle progression. The compound 1-[4-(5-Biphenyl-4-yl-[1,2,4]oxadiazol-3-yl)-benzyl]-5-fluoro-1H-pyrimidine-2,4-dione induced apoptosis through caspase-3/7 activation and S-phase arrest in HT-1080 and A549 cells. The mol. docking showed that compound 1-[4-(5-Biphenyl-4-yl-[1,2,4]oxadiazol-3-yl)-benzyl]-5-fluoro-1H-pyrimidine-2,4-dione activated the caspase-3 by forming a stable protein-ligand complex. In the experiment, the researchers used many compounds, for example, 4-Cyanobenzyl bromide(cas: 17201-43-3Recommanded Product: 4-Cyanobenzyl bromide)

4-Cyanobenzyl bromide(cas: 17201-43-3) can reacts with 2H-tetrazole in the presence of KOH to yield 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile. And it may be used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile.Recommanded Product: 4-Cyanobenzyl bromide

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Nitrile – Wikipedia,
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《Asymmetric Alkylation of Ketones Catalyzed by Engineered TrpB》 was written by Watkins-Dulaney, Ella J.; Dunham, Noah P.; Straathof, Sabine; Turi, Soma; Arnold, Frances H.; Buller, Andrew R.. Electric Literature of C9H7NOThis research focused onTrpB ketone alkylation catalysis propiophenone; asymmetric catalysis; biocatalysis; directed evolution; ketones; nitrogen heterocycles. The article conveys some information:

The β-subunit of tryptophan synthase (TrpB) catalyzes a PLP-mediated β-substitution reaction between indole and serine to form -Trp. A succession of TrpB protein engineering campaigns to expand the enzyme′s nucleophile substrate range has enabled the biocatalytic production of diverse non-canonical amino acids (ncAAs). Here, we show that ketone-derived enolates can serve as nucleophiles in the TrpB reaction to achieve the asym. alkylation of ketones, an outstanding challenge in synthetic chem. We engineered TrpB by directed evolution to catalyze the asym. alkylation of propiophenone and 2-fluoroacetophenone with a high degree of selectivity. In reactions with propiophenone, preference for the opposite product diastereomer emerges over the course of evolution, demonstrating that full control over the stereochem. at the new chiral center can be achieved. The addition of this new reaction to the TrpB platform is a crucial first step toward the development of efficient methods to synthesize non-canonical prolines and other chirally dense nitrogen heterocycles. In the part of experimental materials, we found many familiar compounds, such as 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Electric Literature of C9H7NO)

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.Electric Literature of C9H7NO

Referemce:
Nitrile – Wikipedia,
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In 2022,Ataie, Saeed; Ovens, Jeffrey S.; Tom Baker, R. published an article in Chemical Communications (Cambridge, United Kingdom). The title of the article was 《Solvent-free Zn (NSNO) complex-catalysed dihydroboration of nitriles》.Name: 2-Bromobenzonitrile The author mentioned the following in the article:

N-donors are the most commonly employed Lewis bases in ligand-assisted catalysis. A dimeric zinc complex (Zn-1) employing a tetradentate pyridine-thioether-anilido-aryloxide NSNO ligand (L) effects the quant. conversion of nitriles to the corresponding double hydroborated products at 1 mol% catalyst loading. Variable Time Normalization Anal. kinetic studies showed a first-order dependence with respect to the nitrile, pinacolborane and zinc and clear evidence for catalyst deactivation. A plausible ligand-assisted reaction pathway involves B-H bond activation by the aryloxide (vs. anilido) donor. After reading the article, we found that the author used 2-Bromobenzonitrile(cas: 2042-37-7Name: 2-Bromobenzonitrile)

2-Bromobenzonitrile(cas: 2042-37-7) is used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity. It is commonly employed in reactions that require an electron-rich species to carry out nucleophilic substitution (or addition) reactions.Name: 2-Bromobenzonitrile

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Nitrile – Wikipedia,
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The author of 《Supported organometallic palladium catalyst into mesoporous channels of magnetic MCM-41 nanoparticles for phosphine-free C-C coupling reactions》 were Ghorbani-Choghamarani, Arash; Tahmasbi, Bahman; Hudson, Robert H. E.; Heidari, Ali. And the article was published in Microporous and Mesoporous Materials in 2019. Formula: C7H4BrN The author mentioned the following in the article:

Magnetic MCM-41 nanoparticles were synthesized via Fe3O4-doped into mesoporous channels of MCM-41 nanoparticles and further, a new organometallic complex of palladium was supported on its inner surface (Pd-imi@MCM-41/Fe3O4). This immobilized catalyst was applied as highly efficient, heterogeneous and magnetically recoverable nanocatalyst in the various C-C coupling reactions such as Suzuki-Miyaura and Mizoroki-Heck reactions under phosphine-free conditions at atm. pressure. This catalyst has advantages of both magnetic nanoparticles and mesoporous materials. The structure of prepared nanomaterial has been characterized by various techniques such as N2 adsorption-desorption isotherms, TEM, SEM, EDS, WDX, FT-IR, XRD, TGA, ICP, AAS, and VSM. SEM images of this catalyst demonstrate that the particles size are less than 100 nm in diameter VSM curve of the catalyst shows that this catalyst can be recovered using an external magnet; therefore, this catalyst can be reused for several times without significant loss of its catalytic efficiency or palladium leaching. Also, all products were obtained in high TON and TOF numbers, which reveals this catalyst has high activity and selectivity in described coupling reactions. Heterogeneity and stability of this nanocatalyst were confirmed by hot filtration test and AAS technique.4-Bromobenzonitrile(cas: 623-00-7Formula: C7H4BrN) was used in this study.

4-Bromobenzonitrile(cas: 623-00-7) has been used in the synthesis of 4-iodobenzonitrile via photo-induced aromatic Finkelstein iodination reaction.Formula: C7H4BrN 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.

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Nitrile – Wikipedia,
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In 2017,Mi, Rui-Jie; Sun, Jing; Kuhn, Fritz E.; Zhou, Ming-Dong; Xu, Zhaoqing published 《A meta-selective-C-H alkenylation of phenol-derivatives employing a traceless organosilicon template》.Chemical Communications (Cambridge, United Kingdom) published the findings.Electric Literature of C8H6BrN The information in the text is summarized as follows:

A traceless O-benzeneacetonitrile silyl template-directed meta-selective-C-H Heck alkenylation of phenols was realized with good yields and high selectivities. Etherification of phenol with 3-cyanomethylphenylsilyl substituents gives the directing template, 3-R2C(CN)C6H4SiiPr2OC6H4R1 (R1 = Me, MeO, halo, CF3, MeO2C), which undergoes meta-regioselective palladium-catalyzed Heck alkenylation with Et acrylate, giving cinnamates 3-R2C(CN)C6H4SiiPr2OC6H3R1-3-CH:CHCO2Et; the latter can be easily deprotected, leaving hydroxycinnamates 3-HOC6H3R1CH:CHCO2Et. The template was readily removable through F–promoted O-Si cleavage under extremely mild conditions or recyclable through a p-TSA catalyzed process. The product was successfully applied in the preparation of a series of meta-alkenylated aromatic compounds In the experiment, the researchers used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Electric Literature of C8H6BrN)

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.Electric Literature of C8H6BrN

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Li, Haoyu; Liu, Yuliang; Chiba, Shunsuke published their research in Chemical Communications (Cambridge, United Kingdom) in 2021. The article was titled 《Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis》.Formula: C7H3BrFN The article contains the following contents:

A protocol for anti-Markovnikov hydroarylation of alkenes, e.g., 2,3-dihydrofuran with aryl halides ArX (Ar = (4-CO2CH3)C6H4, 2-naphthyl, 5-cyanothiophen-2-yl, etc.; X = Br, Cl) has been developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light. The results came from multiple reactions, including the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Formula: C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Formula: C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Cobalt-Catalyzed Cross-Coupling of Functionalized Alkylzinc Reagents with (Hetero)Aryl Halides》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Lutter, Ferdinand H.; Grokenberger, Lucie; Spiess, Philipp; Hammann, Jeffrey M.; Karaghiosoff, Konstantin; Knochel, Paul. HPLC of Formula: 105942-08-3 The article mentions the following:

A combination of 10% CoCl2 and 20% 2,2′-bipyridine ligands enables cross-coupling of functionalized primary and secondary alkylzinc reagents RZnY (R = 3-phenylpropyl, 3-(2,5-dimethyl-1H-pyrrol-1-yl)propyl, cyclopropyl, etc.; Y = Cl, Br) with various (hetero)aryl halides R1X (R1 = 5-cyanopyridin-2-yl, quinolin-2-yl, pyrimidin-2-yl, etc.; X = Cl, Br). Couplings with 1,3- and 1,4-substituted cycloalkylzinc reagents R2ZnI (R2 = 3-methylcyclohexyl, 4-(1H-pyrrol-1-yl)cyclohexyl, (4R,4aS,6R,8aR)-4,4a-dimethyl-6-(propan-2-yl)-decahydronaphthalen-2-yl, etc.) proceeded diastereoselectively leading to functionalized heterocycles R1R2 with high diastereoselectivities of up to 98:2. Furthermore, alkynyl bromides R3CCBr (R3 = Ph, tris(propan-2-yl)silyl) react with primary and secondary alkylzinc reagents RZnY (R = 2-(1,3-dioxan-2-yl)ethyl, 4-phenylcyclohexyl; Y = Cl, I) providing the alkylated alkynes RCCR3. In addition to this study using 4-Bromo-2-fluorobenzonitrile, there are many other studies that have used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3HPLC of Formula: 105942-08-3) was used in this study.

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.HPLC of Formula: 105942-08-3 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Hendrick, Charles E.; Bitting, Katie J.; Cho, Seoyoung; Wang, Qiu published 《Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation》.Journal of the American Chemical Society published the findings.Product Details of 105942-08-3 The information in the text is summarized as follows:

Arene amination is achieved by site-selective C-H zincation followed by copper-catalyzed coupling with O-benzoylhydroxylamines under mild conditions. Key to this success is ortho-zincation mediated by lithium amidodiethylzincate base that is effective for a wide range of arenes, including nonactivated arenes bearing simple functionalities such as fluoride, chloride, ester, amide, ether, nitrile, and trifluoromethyl groups as well as heteroarenes including indole, thiophene, pyridine, and isoquinoline. An analogous C-H azidation is also accomplished using azidoiodinane for direct introduction of a useful azide group onto a broad scope of arenes and heteroarenes. These new transformations offer rapid access to valuable and diverse chem. space of aminoarenes. Their broad applications in organic synthesis and drug discovery are demonstrated in the synthesis of novel analogs of natural product (-)-nicotine and antidepressant sertraline by late-stage amination and azidation reactions. After reading the article, we found that the author used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Product Details of 105942-08-3)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Product Details of 105942-08-3 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Recommanded Product: 2-BromobenzonitrileIn 2022 ,《Scalable, Chemoselective Nickel Electrocatalytic Sulfinylation of Aryl Halides with SO2》 was published in Angewandte Chemie, International Edition. The article was written by Lou, Terry Shing-Bong; Kawamata, Yu; Ewing, Tamara; Correa-Otero, Guillermo A.; Collins, Michael R.; Baran, Phil S.. The article contains the following contents:

The sulfonyl fluorides ArSO2F [Ar = 2-MeOC6H4, 4-FC6H4, 3,5-di-MeC6H3, etc.] were synthesized via electrochem. sulfinylation and fluorination of aryl iodides and bromides through aryl sulfinate intermediate using an inexpensive Ni-electrocatalytic protocol. The reaction exhibited a broad scope, used stock solution of simple SO2 as sulfur source, and could be scaled up in batch and recycle flow settings. The limitations of this reaction were clearly shown and put into context by benchmarking with state-of-the-art Pd-based methods. The experimental process involved the reaction of 2-Bromobenzonitrile(cas: 2042-37-7Recommanded Product: 2-Bromobenzonitrile)

2-Bromobenzonitrile(cas: 2042-37-7) belongs to a group of ortho-substituted bromobenzenes that have varying hepatotoxicity effects in the presence of rat liver microsomes in vitro. 2-Bromobenzonitrile is also used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity.Recommanded Product: 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts