Tag: 100-200

Peng, Yi; Oestreich, Martin published an article in 2022. The article was titled 《B(C6F5)3-Catalyzed Reductive Denitrogenation of Benzonitrile Derivatives》, and you may find the article in Organic Letters.SDS of cas: 1194-02-1 The information in the text is summarized as follows:

A B(C6F5)3-catalyzed reductive denitrogenation of aromatic nitriles ArCN (Ar = 4-fluorophenyl, phenanthren-9-yl, 1-benzothiophen-5-yl, etc.) is reported, achieving the metal-free transformation of a cyano into a Me group in a single synthetic operation. Tris(phenylsilyl)amine is liberated as the nitrogen-containing byproduct. On the basis of control experiments as well as a NMR spectroscopic anal., SN1-type mechanism involving a trisilylammonium ion as a key intermediate is proposed. In the experimental materials used by the author, we found 4-Fluorobenzonitrile(cas: 1194-02-1SDS of cas: 1194-02-1)

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《A Complementary C-H Functionalization Mode of Benzoylacetonitriles: Computer-Augmented Study of a Regio- and Stereoselective Synthesis of Functionalized Benzofulvenes》 was published in Organic Letters in 2020. These research results belong to Song, Xia; Do Doan, Bao Nguyen; Zhang, Xinying; Lee, Richmond; Fan, Xuesen. Category: nitriles-buliding-blocks The article mentions the following:

A highly regio- and stereoselective synthesis of functionalized benzofulvenes via Rh(III)-catalyzed cascade reactions of benzoyl acetonitrile/methylsulfone/acetate with propargyl alcs. is presented herein. Mechanistic modeling performed with d. functional theory (DFT) calculations suggested that the hydroxyl group and CsOAc played important roles in mediating the 5-membered ring cyclization by forming a very thermodynamically stable Rh(III) intermediate. Another remarkable feature of this transformation is its excellent stereoselectivity in that only E-isomers are obtained. In the experiment, the researchers used many compounds, for example, 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Category: nitriles-buliding-blocks)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Zheng, Haoteng; Xiao, Qinjie; Mao, Feiying; Wang, Anming; Li, Mu; Wang, Qiuyan; Zhang, Pengfei; Pei, Xiaolin published an article in RSC Advances. The title of the article was 《Programing a cyanide-free transformation of aldehydes to nitriles and one-pot synthesis of amides through tandem chemo-enzymatic cascades》.Safety of 2-Bromobenzonitrile The author mentioned the following in the article:

In this work, a greener chemo-enzymic cascade to synthesize alky and aryl nitriles RCN (R = Ph, Bn, pentyl, furan-2-yl, etc.) from readily accessible aldehydes RCHO, that were further transformed into corresponding amides RC(O)NH2 via an artificial enzyme cascade was reported. A biphasic reaction system was designed to bridge chem. synthesis and enzymic catalysis through simple phase separation The biphasic system mainly perfectly avoided the inactivation of hydroxylamine on aldoxime dehydratase from Pseudomonas putida (OxdF1) and nitrile hydratase from Aurantimonas manganoxydans ATCC BAA-1229 (NHase1229). For the synthesis of various nitriles, moderate isolation yields of approx. 60% were obtained by the chemo-enzymic cascade. Interestingly, two seemingly conflicting reactions of dehydration and hydration were sequentially proceeded to synthesize amides by the synergistic catalysis of OxdF1 and NHase1229 in E. coli cells. An isolation yield of approx. 62% was achieved for benzamide at the one-liter scale. In addition, the shuttle transport of substrates and products between two phases is convenient for the product separation and n-hexane recycling. Thus, the chemo-enzymic cascade shows a potential application in the cyanide-free and large-scale synthesis of nitriles and amides. In the part of experimental materials, we found many familiar compounds, such as 2-Bromobenzonitrile(cas: 2042-37-7Safety of 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.Safety of 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Plakas, Konstantinos; Kalogirou, Andreas S.; Kourtellaris, Andreas; Koutentis, Panayiotis A. published an article in Molbank. The title of the article was 《Reaction of 4,5-Dichloro-1,2,3-dithiazolium Chloride with 2-(Phenylsulfonyl)acetonitrile》.Recommanded Product: 614-16-4 The author mentioned the following in the article:

The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with nitriles (1 equiv) in the presence of pyridine (2 equiv) gave S-(3-chloro-5-cyanoisothiazol-4-yl)benzenesulfonothioate I in 19% and (Z)-2-(5H-1,2,3-dithiazol-5-ylidene)-2-acetonitriles II [R = CN, CO2Me, CO2Et, etc.] were reported. The compounds were fully characterized and the mechanistic rationale was proposed for the formation of the benzensulfonate. In addition to this study using 3-Oxo-3-phenylpropanenitrile, there are many other studies that have used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Recommanded Product: 614-16-4) was used in this study.

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.Recommanded Product: 614-16-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Jia, Fan; He, Jing; Wei, Yueting; Liu, Yan; Gu, Yanlong; Vaccaro, Luigi; Liu, Ping published an article in Molecular Catalysis. The title of the article was 《C4-Sulfenylation of 4-iodine-1H-pyrazole-5-amine with arylsulfonyl hydrazide in water》.Category: nitriles-buliding-blocks The author mentioned the following in the article:

A C4-sulfenylation of 4-iodine-1H-pyrazole-5-amine with arylsulfonyl hydrazide in water was developed. A series of C4-sulfenylated products I [R = t-Bu, Ph, 4-ClC6H4, etc.; Ar = Ph, 4-MeC6H4, 3-BrC6H4, etc.] were obtained in moderate to excellent yields. This protocol featured green reaction conditions (metal-free, water as the solvent, in the air), odorless and easily available sulfur reagent, broad substrate scope as well as gram-scale synthesis. Mechanistic studies showed that the in-situ formation of iodine from 4-iodine-1H-pyrazole-5-amine in the presence of aryl sulfonyl hydrazides was the key to the C4-Sulfenylation. After reading the article, we found that the author used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Category: nitriles-buliding-blocks)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Xue, Gaijun; Xie, Fukai; Liang, Hongliang; Chen, Guoliang; Dai, Wen published an article in Organic Letters. The title of the article was 《Copper-Catalyzed Oxidative C-C Bond Cleavage of Alkyl-(Hetero)arenes Enabling Direct Access to Nitriles》.Name: 4-Fluorobenzonitrile The author mentioned the following in the article:

The cleavage and functionalization of C-C bonds has emerged as a powerful tool for discovery of new transformations. Herein, authors report a protocol that enables direct synthesis of nitriles via copper-catalyzed oxidative cleavage and cyanation of C-C bonds in a wide variety of multicarbon alkyl-substituted (hetero)arenes. Detailed mechanistic studies reveal that a tandem oxidative process is involved in this transformation. In addition to this study using 4-Fluorobenzonitrile, there are many other studies that have used 4-Fluorobenzonitrile(cas: 1194-02-1Name: 4-Fluorobenzonitrile) 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.Name: 4-Fluorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Electrochemical Synthesis of β-Ketonitriles from Aryl Methyl Ketones》 was written by Yavari, Issa; Shaabanzadeh, Sina; Sheikhi, Sara. Recommanded Product: 614-16-4 And the article was included in ChemistrySelect in 2020. The article conveys some information:

A synthesis of β-ketonitriles ArC(O)CH2CN (Ar = Ph, 4-chlorophenyl, naphthalen-2-yl, etc.) by cyanation of aryl Me ketones ArC(O)CH3 with two completely distinct sources of cyanide, namely Me3SiCN and KCN, under metal- and oxidant-free electrochem. anodic oxidation conditions is described. In this approach, a range of β-ketonitriles can be obtained in good yields. This conversion is facilitated by I2, generated in situ from electrochem. oxidation of iodide ion to afford the β-ketonitriles. This environmentally benign method is more convenient and practical compared to previous approaches. In the part of experimental materials, we found many familiar compounds, such as 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Recommanded Product: 614-16-4)

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.Recommanded Product: 614-16-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Phenanthrene Synthesis by Palladium(II)-Catalyzed γ-C(sp2)-H Arylation, Cyclization, and Migration Tandem Reaction》 were Gou, Bo-Bo; Yang, Hui; Sun, Huai-Ri; Chen, Jie; Wu, Junliang; Zhou, Ling. And the article was published in Organic Letters in 2019. SDS of cas: 31938-07-5 The author mentioned the following in the article:

Phenanthrene is an important structural motif in chem. and materials science, and many synthetic routes have been developed to construct its skeleton. However, synthesis of unsym. phenanthrenes remains a challenge. Here, an efficient one-pot tandem reaction for the preparation of phenanthrenes via sequential γ-C(sp2)-H arylation, cationic cyclization, dehydration, and 1,2-migration was developed. A wide range of sym. and unsym. phenanthrenes with diversified functional groups were synthesized with good to excellent yields. In the experiment, the researchers used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5SDS of cas: 31938-07-5)

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Design, synthesis and biological evaluation of pentacyclic triterpene derivatives: optimization of anti-ABL kinase activity》 were Ciftci, Halil I.; Radwan, Mohamed O.; Ozturk, Safiye E.; Ulusoy, N. Gokce; Sozer, Ece; Ellakwa, Doha E.; Ocak, Zeynep; Can, Mustafa; Ali, Taha F. S.; Abd-Alla, Howaida I.; Yayli, Nurettin; Tateishi, Hiroshi; Otsuka, Masami; Fujita, Mikako. And the article was published in Molecules in 2019. Application In Synthesis of 4-Cyanobenzyl bromide The author mentioned the following in the article:

Imatinib, an Abelson (ABL) tyrosine kinase inhibitor, is a lead mol.-targeted drug against chronic myelogenous leukemia (CML). To overcome its resistance and adverse effects, new inhibitors of ABL kinase are needed. Our previous study showed that the benzyl ester of gypsogenin (1c), a pentacyclic triterpene, has anti-ABL kinase and a subsequent anti-CML activity. To optimize its activities, benzyl esters of carefully selected triterpenes (PT1-PT6), from different classes comprising oleanane, ursane and lupane, and new substituted benzyl esters of gypsogenin (GP1-GP5) were synthesized. All of the synthesized compounds were purified and charachterized by different spectroscopic methods. Cytotoxicity of the parent triterpenes and the synthesized compounds against CML cell line K562 was examined; revealing three promising compounds PT5, GP2 and GP5 (IC50 5.46, 4.78 and 3.19 microM, resp.). These compounds were shown to inhibit extracellular signal-regulated kinase (ERK) downstream signaling, and induce apoptosis in K562 cells. Among them, PT5 was identified to have in vitro activity (IC50 = 1.44 microM) against ABL1 kinase, about sixfold of 1c, which was justified by mol. docking. The in vitro activities of GP2 and GP5 are less than PT5, hence they were supposed to possess other more mechanisms of cytotoxicity. In general, our design and derivatizations resulted in enhancing the activity against ABL1 kinase and CML cells. The experimental part of the paper was very detailed, including the reaction process of 4-Cyanobenzyl bromide(cas: 17201-43-3Application In Synthesis of 4-Cyanobenzyl bromide)

4-Cyanobenzyl bromide(cas: 17201-43-3) is an important intermediate for pharmaceutical production. It can be used for the synthesis of a series of piperidine-linked aromatic diimidazolines, which have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii (PCP) drug, Pentamidine.Application In Synthesis of 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Enamine Catalytic Annulation of Azonaphthalenes: An Access to Indole Derivatives》 were Zhao, Hanhui; Yuan, Huijun; Zhang, Yanru; Li, Rongshi; Li, Wenjun. And the article was published in Organic Letters in 2019. Electric Literature of C9H7NO The author mentioned the following in the article:

The secondary-amine mediated [3 + 2] annulation of azonaphthalenes with aldehydes and ketones is described for the first time, which provides an alternative protocol for the synthesis of indole derivatives It features a cheap and readily available catalyst, a broad scope of reactants, very mild reaction conditions, and high efficiency. Significantly different from the transition-metal-mediated processes, the enamine activation represents the first organic base-catalytic protocol for indole synthesis.3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Electric Literature of C9H7NO) was used in this study.

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,
Nitriles – Chemistry LibreTexts