o-Acylbenzonitriles: Synthesis and Heterocyclization under Acid Hydrolysis of the Cyano Group

Mochalov, S. S.; Федотов, А. Н.; Трофимова, Е. В.; Зефиров, Н. С.

doi:10.1134/s1070428018030065

Cited by 9 publications

(4 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Accordingly, we have recently reported efficient cascade reactions of 2‐acetylbenzonitriles in combination with a wide range of nucleophiles (Scheme ) . This preliminary investigation allowed the obtaining of new 3,3‐disubstituted isoindolinones belonging to a privileged class of heterocyclic compounds known for the wide range of biological activities . Despite the increased steric hindrance and the lower electrophilicity of the carbonyl group, we were interested to investigate the reactivity of 2‐cyanobenzophenones.…”

Section: Introductionmentioning

confidence: 99%

“…The use of 2‐cyanobenzophenones is neglected in comparison with the number of methodologies utilizing 2‐cyanobenzaldehydes ,. This lack can also be attributed to the limited number of methodologies for their synthesis, in which inefficient Rosenmund‐VonBraun or Sandmayer reactions have been utilized for the introduction of the cyano group, requiring very harsh reaction conditions. Accordingly, another aim of the present work is related to the necessity to develop direct and more efficient strategies for the access to 2‐cyanobenzophenones (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthetic Strategies and Cascade Reactions of 2‐Cyanobenzophenones for the Access to Diverse 3,3‐Disubstituted Isoindolinones and 3‐Aryl‐3‐Hydroxyisoindolinones

et al. 2019

View full text Add to dashboard Cite

Herein we report new methodologies for the synthesis of the challenging ketones 2‐cyanobenzophenones, based on Suzuki‐Miyaura type cross‐coupling reactions and very mild oxidation of 2‐benzylbenzonitriles. The investigation of the reactivity of the obtained ketones highlighted a very good electrophilicity in the presence of mild carbon‐ and hetero‐nucleophiles, allowing the synthesis of 3,3‐disubstituted isoindolin‐1‐ones. All the developed methodologies are highly efficient and tolerate combinations of functional groups present on both the aromatic rings.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthetic Strategies and Cascade Reactions of 2‐Cyanobenzophenones for the Access to Diverse 3,3‐Disubstituted Isoindolinones and 3‐Aryl‐3‐Hydroxyisoindolinones

et al. 2019

View full text Add to dashboard Cite

show abstract

“…The changes in O content could be attributed to the enhance hydrolysis of terminal amide into carboxylic groups, with the help of acidic FeCl 3 hydrates. [ 32 ] The deconvolution of O spectra confirms two chemical states where the C─O configuration tends to have a positive relationship with the feed amount of iron (Figure S1c, Supporting Information). The change of O content contrarily leads to the drop of N content from 18 to 10 at.% (Figure 1g).…”

Section: Resultsmentioning

confidence: 87%

Solvothermal Synthesis and Pyrolysis Toward Heteroatom‐Doped Carbon Microspheres for Zinc‐Ion Hybrid Capacitors

Huang,

Gu,

et al. 2023

Small

View full text Add to dashboard Cite

Heteroatom‐doped porous carbon materials have investigated to promote the energy density of zinc‐ion hybrid capacitors (ZICs). Yet, the quest for high‐performance carbon materials or cathodes brings to light the question of which dopants facilitate fast energy storage kinetics and various types of pseudocapacitive reactions. Investigation of carbon materials with precise quantitative dopants as the key variable represents an effective appropriate approach to comprehending the intricate role of dopants in energy storage areas. Here, a straightforward solvothermal strategy is demonstrated for a variety of pristine and iron‐incorporated polymer microspheres, used as precursors for durable spherical carbons intended for cathode applications in ZICs. The strategy effectively governs the incorporation of dopants within the carbon materials, whilewhile maintaining consistent morphology, microtexture, and pore structure across different carbon variations. The synergistic effect of various dopants enhance the pseudocapacitance and facilitate the ion storage process. In consequence, the optimal cathode delivers considerable capacity (178.8 mAh g−1 at 0.5 A g−1), good energy density (120.2 Wh kg−1 at 336 W kg−1), and excellent cycling stability (101.5% capacity retention at 35 000 cycles). The demonstration showcases a viable method for crafting carbon materials with precise dopants to accommodate the zinc anode, thus enabling high‐capacity and high‐energy ZICs.

show abstract

“…In this context, we have developed efficient cascade reactions of 2-acetylbenzonitriles, which react with a range of nucleophiles to afford useful 3,3-disubstituted isoindolinones in the presence of K 2 CO 3 [8]. The difficult accessibility to 2-acylbenzonitriles is also a limitation, from which results few synthetic applications [8][9][10]. Hence, the aim of the present work is to develop viable synthesis of these compounds and preliminary investigation of the reactivity of 2-acylbenzonitriles with nitromethane in the presence of chiral organocatalytic systems.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Organocatalytic Asymmetric Nitro-aldol Initiated Cascade Reactions of 2-Acylbenzonitriles Leading to 3,3-Disubstituted Isoindolinones

et al. 2019

View full text Add to dashboard Cite

In this work, we investigated two strategies for the synthesis of the challenging ketones 2-acylbenzonitriles and we report their use as electrophiles in asymmetric organocatalytic cascade reactions with nitromethane. Promising results were obtained in the presence of chiral bifunctional ammonium salts under phase transfer conditions, which led to novel 3,3-disubstituted isoindolinones in quantitative yields and moderate enantioselectivity.

show abstract

o-Acylbenzonitriles: Synthesis and Heterocyclization under Acid Hydrolysis of the Cyano Group

Cited by 9 publications

References 13 publications

Synthetic Strategies and Cascade Reactions of 2‐Cyanobenzophenones for the Access to Diverse 3,3‐Disubstituted Isoindolinones and 3‐Aryl‐3‐Hydroxyisoindolinones

Synthetic Strategies and Cascade Reactions of 2‐Cyanobenzophenones for the Access to Diverse 3,3‐Disubstituted Isoindolinones and 3‐Aryl‐3‐Hydroxyisoindolinones

Solvothermal Synthesis and Pyrolysis Toward Heteroatom‐Doped Carbon Microspheres for Zinc‐Ion Hybrid Capacitors

Synthesis and Organocatalytic Asymmetric Nitro-aldol Initiated Cascade Reactions of 2-Acylbenzonitriles Leading to 3,3-Disubstituted Isoindolinones

Contact Info

Product

Resources

About