Month: October 2022

《Photoredox-Catalyzed Site-Selective Generation of Carbanions from C(sp3)-H Bonds in Amines》 was written by Murugesan, Kathiravan; Donabauer, Karsten; Narobe, Rok; Derdau, Volker; Bauer, Armin; Koenig, Burkhard. Formula: C43H30F2N4 And the article was included in ACS Catalysis on April 1 ,2022. The article conveys some information:

Herein, activation of a C(sp3)-H bond in the α-position to an amine via a carbanion intermediate was described. In the presence of several α-amine sites, only one specific position was selectively activated. Applying this protocol, the proposed carbanion intermediate was effectively trapped with different electrophiles such as deuterium (D+), tritium (T+), or carbonyl compounds compiling over 50 examples. Further, this methodol. was used to install deuterium or tritium in different drug-derivatives (>10 drugs) at a selected position in a late-stage functionalization. In addition, the protocol was suitable for a gram-scale synthesis, and a detailed mechanistic investigation was carried out to support our hypothesis. The experimental part of the paper was very detailed, including the reaction process of 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile(cas: 1403850-00-9Formula: C43H30F2N4)

2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile(cas: 1403850-00-9) is cyanoarene-based donor-acceptor photocatalyst developed by the Zeitler group. While this catalyst has a balanced redox profile, allowing for its use in a variety of transformations, it stands out as the most reducing catalyst of the family.Formula: C43H30F2N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Photocatalytic carbanion generation from C-H bonds – reductant free Barbier/Grignard-type reactions》 were Berger, Anna Lucia; Donabauer, Karsten; Koenig, Burkhard. And the article was published in Chemical Science in 2019. Electric Literature of C43H30F2N4 The author mentioned the following in the article:

A redox-neutral method for the generation of carbanions from benzylic C-H bonds in a photocatalytic Grignard-type reaction was reported. The combination of photo- and hydrogen atom transfer (HAT) catalysis enabled the abstraction of a benzylic hydrogen atom, generating a radical intermediate. This radical was reduced in situ by the organic photocatalyst to a carbanion, which was able to react with electrophiles such as aldehydes or ketones, yielding homobenzylic secondary and tertiary alcs. ArCR1R2C(OH)R3R4 [R1 = R2 = H, Me, R1 = H, R2 = Me; R3 = R4 = Me, Et, n-Bu, R3 = H, Me, R4 = Me, Et, i-Pr, etc; Ar = 2-thienyl, Ph, 4-MeOC6H4, etc.]. In the experiment, the researchers used many compounds, for example, 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile(cas: 1403850-00-9Electric Literature of C43H30F2N4)

2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile(cas: 1403850-00-9) is cyanoarene-based donor-acceptor photocatalyst developed by the Zeitler group. While this catalyst has a balanced redox profile, allowing for its use in a variety of transformations, it stands out as the most reducing catalyst of the family.Electric Literature of C43H30F2N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2010,Liu, Yang; Huang, Liping; Xie, Fuchun; Hu, Youhong published 《Base-Promoted One-Pot Tandem Reaction of 3-(1-Alkynyl)chromones under Microwave Irradiation to Functionalized Amino-Substituted Xanthones》.Journal of Organic Chemistry published the findings.Synthetic Route of C8H6BrN The information in the text is summarized as follows:

A base-promoted one-pot tandem reaction has been developed from 3-(1-alkynyl)chromones, e.g., I, with various acetonitriles to afford functionalized amino-substituted xanthones, e.g., II, under microwave irradiation This tandem process involves multiple reactions, such as Michael addition/cyclization/1,2-addition, without a transition metal catalyst. This method provides an efficient approach to build up natural product-like diversified amino-substituted xanthone scaffolds rapidly.2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Synthetic Route of C8H6BrN) 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.Synthetic Route of C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Sonyanaik, Banoth; Sakram, Boda published 《Design and synthesis of novel substituted 1,8-naphthyridin-2-yl-amide derivatives at ambient temperature and evaluation of their antimicrobial activity》.Heterocyclic Letters published the findings.Application In Synthesis of 2-(3-Bromophenyl)acetonitrile The information in the text is summarized as follows:

A new series of substituted 1,8-naphthyridin-2-yl-amide derivatives I (R1 = H, 3-NO2, 4-Br, etc.; R2 = H, 4-Cl) have been successfully synthesized in good yields at ambient temperature by reaction of various substituted 3-phenyl-1,8-naphthyridin-2-amines with aryl benzoic acids. All the newly synthesized compounds were evaluated for their in vitro antimicrobial activity. All these compounds exhibit good antibacterial and excellent antifungal activity. Among them, compound I (R1 = H, 4-Br, 4-NO2; R2 = 4-Cl) showed remarkable inhibition of antimicrobial activity. The results came from multiple reactions, including the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Application In Synthesis of 2-(3-Bromophenyl)acetonitrile)

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.Application In Synthesis of 2-(3-Bromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Pd(II)-immobilized on a nanoporous triazine-based covalent imine framework for facile cyanation of haloarenes with K4Fe(CN)6》 were Puthiaraj, Pillaiyar; Yu, Kwangsun; Shim, Sang Eun; Ahn, Wha-Seung. And the article was published in Molecular Catalysis in 2019. COA of Formula: C7H4BrN The author mentioned the following in the article:

A porous covalent organic framework incorporated with both imine and triazine functionalities (TPA-TCIF) was synthesized by Schiff-base condensation of 2,4,6-tris(4-aminophenyl)triazine and tris(4-formylphenyl)amine under the solvothermal condition of a 1-butanol:1,2-dichlorobenzene mixture The resulting TPA-TCIF was a highly ordered crystalline network with surface area of 2938 m2 g-1, which was among the highest reported imine-based porous covalent organic frameworks. TPA-TCIF was also stable in water and other organic solvents. Pd(II) was immobilized into TPA-TCIF network and the resultant Pd/TPA-TCIF was tested as a catalyst for the additive-free cyanation of haloarenes with non-toxic K4[Fe(CN)6]. The catalyst showed excellent catalytic activity, and both electron-donating / -withdrawing groups attached to the para- and meta-positions of bromoarenes produced the resp. nitriles with good to excellent yields. The catalyst could be reused up to five times without noticeable loss of activity or catalyst poisoning by cyanide ions during the reaction. In the experiment, the researchers used many compounds, for example, 4-Bromobenzonitrile(cas: 623-00-7COA of Formula: C7H4BrN)

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,COA of 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.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Palladium-catalyzed successive C-H bond arylations and annulations toward the π-extension of selenophene-containing aromatic skeletons》 were Shi, Xinzhe; Mao, Shuxin; Roisnel, Thierry; Doucet, Henri; Soule, Jean-Francois. And the article was published in Organic Chemistry Frontiers in 2019. HPLC of Formula: 2042-37-7 The author mentioned the following in the article:

A modular approach for the synthesis of planar π-extended selenium containing mols. from selenophene has been developed. Different combinations of Pd-catalyzed desulfitative C-H bond arylations with (2-bromo)arylsulfonyl chlorides R-2-BrC6H3SO2Cl (R = H, 4-CF3, 4-F, 5-CF3) and Pd-catalyzed intra- or/and inter-mol. C-H bond arylations with aryl bromides R1Br (R1 = 4-CNC6H4, 5-acetylthiophen-2-yl, 3-F3CC6H4, etc.) allowed the extension of the selenophene-containing aromatic skeleton at the [b]-, [c]- or [b:d]-junctions to give phenanthro[b]selenophenes, e.g. I, phenanthro[c]selenophenes, II (R2 = CN, NO2, OCH3, CF3; R3 = H, CF3) or diphenanthro[b:d]selenophenes III (R4 = H, CF3, CN; R5 = H, CF3). In the experimental materials used by the author, we found 2-Bromobenzonitrile(cas: 2042-37-7HPLC of Formula: 2042-37-7)

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.HPLC of Formula: 2042-37-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Zn-Catalyzed Cyanation of Aryl Iodides》 was published in Journal of Organic Chemistry in 2020. These research results belong to Zhao, Lulu; Dong, Yanan; Xia, Qiangqiang; Bai, Jianfei; Li, Yuehui. COA of Formula: C7H4FN The article mentions the following:

An efficient method for the synthesis of cyanides such as ArCN [Ar = 4-ClC6H4, 4-MeC6H4, 1-naphthyl, etc.] via zinc-catalyzed cyanation of aryl iodides with formamide as cyanogen source was reported. The transformation was promoted by bisphosphine Nixantphos ligand. Under optimized conditions, a variety of electron-donating and electron-withdrawing aryl iodides were converted into the nitrile products ArCN in good to excellent yields. This approach was an exceedingly simple and benign method for the synthesis of aryl nitriles ArCN and was likely to proceed via a dinuclear-Zn concerted catalysis. The experimental part of the paper was very detailed, including the reaction process of 4-Fluorobenzonitrile(cas: 1194-02-1COA of Formula: C7H4FN)

4-Fluorobenzonitrile(cas: 1194-02-1) is used in the synthesis of flurenones, pharmaceutical prerequisites, as well as opiod receptor antagonists.COA of Formula: C7H4FN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《High-Contrast Polymorphic Luminogen Formed through Effect of Tiny Differences in Intermolecular Interactions on the Intramolecular Charge Transfer Process》 was published in Advanced Optical Materials in 2020. These research results belong to Wang, Kang; Xie, Yujun; Liu, Ming; Tao, Wei; Zhang, Hao; Huang, Meidong; You, Jinmao; Liu, Ying; Li, Yunliang; Li, Zhen; Dong, Yong Qiang. Category: nitriles-buliding-blocks The article mentions the following:

Polymorphic luminogens provide the opportunity to disclose relation between the packing patterns and performance of luminogen and facilitate design of high performance luminogens. However, the effect of intramol. charge transfer (ICT) is seldom used to construct luminogens with polymorphs, though the ICT process is very sensitive to microenvironment. In this work, 2-(3-(diphenylamino)-9H-xanthen-9-ylidene)-malononitrile (DPAXM, 1) with donor-acceptor structure exhibits high contrast polymorphism dependent emission due to the effect of tiny differences of intermol. interactions on ICT process. Three crystals of 1 with nearly identical structures emit yellow, orange, and red light with sequentially decreased efficiency which is attributed to ICT process modulated by the tiny differences in intermol. interactions. In addition to ground state study, excited state of the polymorphs is investigated by time-resolved ultrafast transient mid-IR spectroscopy and theor. calculation Nonemissive crystals of 1 can also be obtained. The modulation of ICT effect by intermol. interactions may provide a reference for the mol. design of high-performance luminogens. The results came from multiple reactions, including the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Category: nitriles-buliding-blocks)

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.Category: nitriles-buliding-blocks 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Well-Defined Palladium N-Heterocyclic Carbene Complexes: Direct C-H Bond Arylation of Heteroarenes》 was written by Kumar, Anuj; Kumar, Manoj; Verma, Akhilesh K.. Application In Synthesis of 4-Bromobenzonitrile And the article was included in Journal of Organic Chemistry in 2020. The article conveys some information:

A series of palladium N-heterocyclic carbene (NHC) complexes of type trans-{(NHC)PdCl2L} (L = C5H5N, 3-ClC5H4N, and PPh3) have been developed as efficient precatalysts for direct C-H bond arylation of various heteroarenes. In particular, an in situ generated new NHC ligand derived from {1,3-bis(2,6-diethylphenyl)acenaphtho[1,2-d]imidazolium} chloride is used for the stabilization of the palladium metal center. Among the screened palladium precatalysts, the most active PEPPSI themed complex was successfully employed toward direct C-H bond arylation of various heteroarenes and aryl bromides. A range of functional groups on aryl bromides as well as on heteroarenes sustained throughout the standard reaction conditions for easy access of various arylated heterocyclic compounds Significantly, the utility of the protocol was demonstrated by the effective synthesis of a precursor of raloxifene, a selective estrogen receptor modulator.4-Bromobenzonitrile(cas: 623-00-7Application In Synthesis of 4-Bromobenzonitrile) was used in this study.

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,Application In Synthesis 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

Eldehna, Wagdy M.; El Hassab, Mahmoud A.; Abo-Ashour, Mahmoud F.; Al-Warhi, Tarfah; Elaasser, Mahmoud M.; Safwat, Nesreen A.; Suliman, Howayda; Ahmed, Marwa F.; Al-Rashood, Sara T.; Abdel-Aziz, Hatem A.; El-Haggar, Radwan published an article in 2021. The article was titled 《Development of isatin-thiazolo[3,2-a]benzimidazole hybrids as novel CDK2 inhibitors with potent in vitro apoptotic anti-proliferative activity: Synthesis, biological and molecular dynamics investigations》, and you may find the article in Bioorganic Chemistry.HPLC of Formula: 17201-43-3 The information in the text is summarized as follows:

The present work aims at developing a new set of small mols. featuring the privileged isatin scaffold conjugated with a thiazolo[3,2-a]benzimidazole (TBI) motif through a cleavable hydrazide linker I (R = H, F, Br, OMe and NO2) and II (R = H, Br; R1 = Me, allyl, Bn, etc.) as potential anticancer CDK2 inhibitors. The growth of the two examined cell lines was significantly inhibited by most the prepared hybrids with IC50 ranges; (2.60 +/- 1.47-20.90 +/- 1.17μM, against MDA-MB-231) and (1.27 +/- 0.06-16.83 +/- 0.95μM, against MCF-7). They exerted a significance alteration in the cell cycle progression, in addition to an apoptosis induction within both MDA-MB-231 and MCF-7 cells. Furthermore, I (R = H), I (R = OMe) and II (R = H; R1 = Me) displayed potent CDK2 inhibitory action (IC50 = 96.46 +/- 5.3, 26.24 +/- 1.4 and 42.95 +/- 2.3 nM, resp.). Interestingly, the most potent CDK2 inhibitor I (R = OMe) achieved the best binding score (-11.2 Kcal/mol) and formed the most stable complex with CDK2 enzyme (RMSD = 1.24 Å ) in a 100 ns MD simulation. In addition, the MM-PBSA calculations ascribed the lowest binding free energy to the I (R = OMe)-CDK2 complex (-323.69 +/- 15.17 kJ/mol). Finally, these results suggested hybrid I (R = OMe) as a good candidate for further optimization as promising breast cancer antitumor agent and CDK2 inhibitor. The experimental process involved the reaction of 4-Cyanobenzyl bromide(cas: 17201-43-3HPLC of Formula: 17201-43-3)

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.HPLC of Formula: 17201-43-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts