Category: 614-16-4

《Revision of the Regioselectivity of the Beirut Reaction of Monosubstituted Benzofuroxans with Benzoylacetonitrile. 6-Substituted quinoxaline-2-carbonitrile 1,4- dioxides: Structural Characterization and Estimation of Anticancer Activity and Hypoxia Selectivity》 was written by Buravchenko, Galina I.; Scherbakov, Alexander M.; Korlukov, Alexander A.; Dorovatovskii, Pavel V.; Shchekotikhin, Andrey E.. Name: 3-Oxo-3-phenylpropanenitrileThis research focused ontirapazamine benzofuroxan anticancer agent hypoxia normoxia adenocarcinoma; 6(7)-substituted-3-phenylquinoxaline-2-carbonitrile 1,4-dioxides; Beirut reaction; CIGAR-HMBC method; X-ray structural analysis; antiproliferative activity; hypoxia-selective cytotoxins; structural isomers.. The article conveys some information:

Objective: The preparation, isolation, structure characterization, and screening for anticancer activity of the first representatives of 6-substituted quinoxaline-2-carbonitrile 1,4-dioxides have been described. Materials and Methods: A series of 7- and 6-halogeno-3-phenylquinoxaline-2-carbonitrile 1,4-dioxides was synthesized by the Beirut reaction. The cytotoxicity was assessed by MTT test (72 h incubation) in normoxia (21% O2) and hypoxia (1% O2) conditions. Results: We found that during the Beirut reaction between a benzofuroxan bearing an electron withdrawing group and benzoylacetonitrile in the presence of triethylamine, in addition to well-known 7-substituted quinoxaline-2-carbonitrile 1,4-dioxides 7-11a, the 6-isomers 7-11b are formed. Moreover, the yield of the 6- isomers increased with the increase in the electron-withdrawing character of the substituent. For benzofuroxans with CO2Me and CF3 groups, 6-substituted quinoxaline-2-carbonitrile 1,4-dioxides 10-11b were the major products. Despite similarities in physicochem. and spectroscopic properties, the obtained isomers exhibit considerable differences in their anticancer activity and hypoxia selectivity. Conclusion: Substituents and their electronic effects play a key role in the formation of 7- and 6-substituted quinoxaline-2-carbonitrile 1,4-dioxides in the Beirut reaction and in the cytotoxicity properties of the obtained isomers. The experimental process involved the reaction of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Name: 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.Name: 3-Oxo-3-phenylpropanenitrile

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Nitrile – Wikipedia,
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《Umpolung Strategy with 2-Aminothiophenols: Access to 2-Arylbenzothiazine Derivatives from Alkyl Aryl Ketones》 was published in Advanced Synthesis & Catalysis in 2020. These research results belong to Nguyen, Thanh Binh; Retailleau, Pascal. Application In Synthesis of 3-Oxo-3-phenylpropanenitrile The article mentions the following:

Strong Broensted acids were found to catalyze the oxidative condensation of 2-aminothiophenols with aryl alkyl ketones in DMSO to provide a wide range of complex 2-arylbenzothiazines I [R = H, Cl; R1 = 4-FC6H4, 4-MeC6H4, 2-thienyl, etc.]. With acetophenones, dimeric 2-arylbenzothiazines II [Ar = Ph, 4-FC6H4, 4-ClC6H4, 4-OMeC6H4] were formed. On the other hand, the reaction with propiophenones resulted in 2:1 adducts whereas 1:1 adducts were produced with isobutyrophenones, benzoylacetonitrile and Et benzoylacetate. In addition to this study using 3-Oxo-3-phenylpropanenitrile, there are many other studies that have used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Application In Synthesis of 3-Oxo-3-phenylpropanenitrile) 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.Application In Synthesis of 3-Oxo-3-phenylpropanenitrile

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《Metal-Free and Regioselective Synthesis of Substituted and Fused Chromenopyrrole Scaffolds via the Divergent Reactivity of α-Azido Ketones in Water》 was published in Journal of Organic Chemistry in 2020. These research results belong to Dhanasekar, Elumalai; Kannan, Tharanikkarasu; Venkatesan, Rengarajan; Perumal, Paramasivam Thirumalai; Kamalraja, Jayabal. Safety of 3-Oxo-3-phenylpropanenitrile The article mentions the following:

A green and simple approach was developed for the regioselective synthesis of structurally diverse chromenopyrrole frameworks from 3-formylchromones, active methylenes and α-azido ketones using piperidine as a catalyst in the aqueous medium through a tandem one pot multi-component reaction. Further, the synthesized pyrrole framework was successfully converted into biol. significant 6-azaindole derivatives in simple synthetic transformation. An exciting feature of this synthetic protocol is that the reaction mechanism and formation of the products depend on the nature of the active methylene used. This approach has several advantages such as transition metal-free catalyst, a short reaction time, easy separation, an excellent yield, practically simple execution, high regioselectivity, very good atom economy, low E-factor, and no requirement of toxic solvents and chromatog. purification The experimental part of the paper was very detailed, including the reaction process of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Safety of 3-Oxo-3-phenylpropanenitrile)

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.Safety of 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Yadav, Maruti B.; Jeong, Yeon Tae published their research in Organic & Biomolecular Chemistry in 2021. The article was titled 《A one-pot ring-closure and ring-opening sequence for the cascade synthesis of dihydrofurofurans and functionalized furans》.Formula: C9H7NO The article contains the following contents:

Authors have developed a simple novel ring-closure and ring-opening pathway using an organo-base system for the synthesis of highly substituted dihydrofurofuran and furan frameworks via a triethylamine-catalyzed one-pot three-component reaction. The protocol involved a Knoevenagel and Michael adduct via Paal-Knorr cyclization with aromatic/aliphatic glyoxal and 2-cyanoacetophenone under mild and heating conditions with excellent yields through a simple filtration method. The merits of this methodol., including the use of easily available feedstocks and an inexpensive catalyst, Gram-scale synthesis, wide functional group tolerance, an open-air reaction setup, and no need for workup and column-chromatog. procedures, make the developed methodol. a practical way to access dihydrofurofurans and functionalized furans. After reading the article, we found that the author used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Formula: C9H7NO)

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.Formula: C9H7NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of C9H7NOIn 2022 ,《Lewis Acid-Relayed Singlet Oxygen Reaction with Enamines: Selective Dimerization of Enamines to Pyrrolin-4-ones》 appeared in Journal of the American Chemical Society. The author of the article were Lei, Tao; Cheng, Yuan-Yuan; Han, Xu; Zhou, Chao; Yang, Bing; Fan, Xiu-Wei; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu. The article conveys some information:

Singlet oxygen (1O2)-mediated oxidation represents an attractive strategy for incorporation of oxygen atoms from air under mild and environmentally benign conditions. However, the 1O2 reaction with enamine suffers from fragmentation, leading to very unsuccessful transformation. Here, Lewis acid is introduced to intercept [2 + 2] or “”ene”” reaction intermediates of the 1O2 reaction and enables oxidative dimerization of enamines to produce pyrrolin-4-ones in good to excellent yields. Mechanistic studies reveal the formation of the imino ketone intermediate from the interaction of 1O2 and enamine, which is able to interact with Lewis acid, relaying the 1O2 reaction in enamine chem. For the first time, selective cross-dimerization of two different enamines is achieved. Due to the advantages of mild conditions, high chemoselectivity, and up to 99% yield, a promising strategy has been developed for synthesizing aza-heterocycles under ambient conditions, which can be further applied for the synthesis of imidazolone, quinoxaline, and highly functionalized imine. In the experiment, the researchers used many compounds, for example, 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Synthetic Route 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.Synthetic Route of C9H7NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Synthesis of α-Ketoamides from β-Ketonitriles and Primary Amines: A Catalyst-Free Oxidative Decyanation-Amidation Reaction》 were Zhang, Ya-Kai; Wang, Bin. And the article was published in European Journal of Organic Chemistry in 2019. Recommanded Product: 3-Oxo-3-phenylpropanenitrile The author mentioned the following in the article:

AN oxidative decyanation-amidation of β-ketonitriles and primary amines readily occurs using hydrogen peroxide sodium carbonate adduct (Na2CO3·1.5H2O2), K2CO3, and 1,4-dioxane. This reaction affords α-ketoamides under mild conditions without the need of a catalyst. In the experiment, the researchers used many compounds, for example, 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Recommanded Product: 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.Recommanded Product: 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhu, Ruiheng; Reddy, Ramesh; Ding, Man; Xu, Ming; Deng, Chaoyi; Tadayon, Sam; Li, Hui; Depew, Kristopher; Lane, Benjamin published an article in 2021. The article was titled 《Development and Scale-Up of a Continuous Manufacturing Process for a Hydrazine Condensation Reaction》, and you may find the article in Organic Process Research & Development.COA of Formula: C9H7NO The information in the text is summarized as follows:

The development of a continuous manufacturing process for a hydrazine condensation reaction at high temperature was reported. This continuous process represented a safer approach to manufacture 3-phenyl-1H-pyrazol-5-amine at scale and exhibited better impurity control compared to a traditional batch process. A controlled crystallization allowed consistently low levels of residual hydrazine (<20 ppm) in isolated solids for further processing to final drug substance. The scalability and robustness of the continuous process was demonstrated at 3 kg scale with a throughput of 0.5 kg/h.3-Oxo-3-phenylpropanenitrile(cas: 614-16-4COA of Formula: 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.COA of Formula: C9H7NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kumar Mehra, Manish; Malik, Monika; Kumar, Bintu; Kumar, Dalip published an article in 2021. The article was titled 《Chemoselective Cu-catalyzed synthesis of diverse N-arylindole carboxamides, β-oxo amides and N-arylindole-3-carbonitriles using diaryliodonium salts》, and you may find the article in Organic & Biomolecular Chemistry.Reference of 3-Oxo-3-phenylpropanenitrile The information in the text is summarized as follows:

Chemoselective copper-catalyzed synthesis of diverse N-arylindole-3-carboxamides, β-oxo amides and N-arylindole-3-carbonitriles from readily accessible indole-3-carbonitriles, α-cyano ketones and diaryliodonium salts has been developed. Diverse N-arylindole-3-carboxamides and β-oxo amides were successfully achieved in high yields under copper-catalyzed neutral reaction conditions, and the addition of an organic base (DIPEA) resulted in a completely different selectivity pattern to produce N-arylindole-3-carbonitriles. Moreover, the importance of the developed methodol. was realized by the synthesis of indoloquinolones and N-((1H-indol-3-yl)methyl)aniline and by a single-step gram-scale synthesis of the naturally occurring cephalandole A analog. In the part of experimental materials, we found many familiar compounds, such as 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

《Triarylamine-Pyridine-Carbonitriles for Organic Light-Emitting Devices with EQE Nearly 40%》 was written by Chen, Yi-Kuan; Jayakumar, Jayachandran; Hsieh, Chia-Min; Wu, Tien-Lin; Liao, Chun-Cheng; Pandidurai, Jayabalan; Ko, Chang-Lun; Hung, Wen-Yi; Cheng, Chien-Hong. Safety of 3-Oxo-3-phenylpropanenitrileThis research focused ontriarylamine pyridine carbonitrile organic light emitting device photoluminescence; external quantum efficiency of nearly 40%; molecular orientation; operational stability; organic light-emitting diodes; pyridine-carbonitrile; thermally activated delayed fluorescence; triphenylamine. The article conveys some information:

Highly efficient thermally activated delayed fluorescence (TADF) mols. are in urgent demand for solid-state lighting and full-color displays. Here, the design and synthesis of three triarylamine-pyridine-carbonitrile-based TADF compounds, TPAPPC, TPAmPPC, and tTPAmPPC, are shown. They exhibit excellent photoluminescence quantum yields of 79-100% with small ΔEST values, fast reverse intersystem crossing (RISC), and high horizontal dipole ratios (Θ// = 86-88%) in the thin films leading to the enhancement of device light outcoupling. Consequently, a green organic light-emitting diode (OLED) based on TPAmPPC shows a high average external quantum efficiency of 38.8 ± 0.6%, a current efficiency of 130.1 ± 2.1 cd A-1, and a power efficiency of 136.3 ± 2.2 lm W-1. The highest device efficiency of 39.8% appears to be record-breaking among TADF-based OLEDs to date. In addition, the TPAmPPC-based device shows superior operation lifetime and high-temperature resistance. It is worth noting that the TPA-PPC-based materials have excellent optical properties and the potential for making them strong candidates for TADF practical application. In the experiment, the researchers used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Safety 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.Safety of 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Angewandte Chemie, International Edition included an article by Li, Xiangdong; Golz, Christopher; Alcarazo, Manuel. Product Details of 614-16-4. The article was titled 《5-(Cyano)dibenzothiophenium Triflate: A Sulfur-Based Reagent for Electrophilic Cyanation and Cyanocyclizations》. The information in the text is summarized as follows:

The synthesis of 5-(cyano)dibenzothiophenium triflate 9 (I.OTf-), prepared by activation of dibenzo[b,d]thiophene-5-oxide with Tf2O and subsequent reaction with TMSCN is reported, and its reactivity as electrophilic cyanation reagent evaluated. The scalable preparation, easy handling and broad substrate scope of the electrophilic cyanation promoted by 9, which includes amines, thiols, silyl enol ethers, alkenes, electron rich (hetero)arenes and polyaromatic hydrocarbons, illustrate the synthetic potential of this reagent. Importantly, Lewis acid activation of the reagent is not required for the transfer process. We addnl. report herein biomimetic cyanocyclization cascade reactions, which are not promoted by typical electrophilic cyanation reagents, demonstrating the superior ability of 9 to trigger challenging transformations. In the part of experimental materials, we found many familiar compounds, such as 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Product Details of 614-16-4)

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.Product Details of 614-16-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts