Electrochemical Cyclotrimerization of Cyanoacetic Ester into trans-1,2,3-Tricyanocyclopropane-1,2,3-Tricarboxylate

Elinson, Michaïl N.; Lizunova, T. L.; Dekaprilevich, M. O.; Struchkov, Yurii T.; Nikishin, G. I.

doi:10.1070/mc1993v003n05abeh000283

Cited by 23 publications

(8 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The yields and scope of tetramethylpropane-1,1,3,3-tetracarboxylates were improved on by Elinson and co-workers, 1089 and Okimoto and co-workers expand this transformation to the cyclization of 1,3-diaroylpropanes. 1090 This strategy can also be applied to the cyclotrimerization of dimethylmalonate 1091 and ethylcyanoacetate 1092 derivatives as the coupling partner to form spirocyclopropylbarbiturates. 1104 The first disclosure of a photoredox-catalyzed alkene cyclopropanation using 1,1-dihaloreagents was reported by Guo in 2015 using dibromomalonates (R1, Scheme 109) as the one-carbon synthon and activated styrenes as the reaction partner.…”

Section: Deprotection Via Redox Chemistriesmentioning

confidence: 99%

“…The yields and scope of tetramethylpropane-1,1,3,3-tetracarboxylates were improved on by Elinson and co-workers, and Okimoto and co-workers expand this transformation to the cyclization of 1,3-diaroylpropanes . This strategy can also be applied to the cyclotrimerization of dimethylmalonate and ethylcyanoacetate through a repeating stepwise deprotonation–halogenation–halogen elimination sequence culminating in cyclopropane synthesis. Applying halide redox mediators to the coupling of malonic acid derivatives and Michael acceptors eliminates the need for direct reduction of substrate as the transformation proceeds mechanistically similar to McCoy-type cyclopropanation.…”

Section: Synthetic Comparisons Between Photoredox Catalysis and Elect...mentioning

confidence: 99%

See 1 more Smart Citation

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

2021

View full text Add to dashboard Cite

Redox processes are at the heart of synthetic methods that rely on either electrochemistry or photoredox catalysis, but how do electrochemistry and photoredox catalysis compare? Both approaches provide access to high energy intermediates (e.g., radicals) that enable bond formations not constrained by the rules of ionic or 2 electron (e) mechanisms. Instead, they enable 1e mechanisms capable of bypassing electronic or steric limitations and protecting group requirements, thus enabling synthetic chemists to disconnect molecules in new and different ways. However, while providing access to similar intermediates, electrochemistry and photoredox catalysis differ in several physical chemistry principles. Understanding those differences can be key to designing new transformations and forging new bond disconnections. This review aims to highlight these differences and similarities between electrochemistry and photoredox catalysis by comparing their underlying physical chemistry principles and describing their impact on electrochemical and photochemical methods.

show abstract

Section: Deprotection Via Redox Chemistriesmentioning

confidence: 99%

Section: Synthetic Comparisons Between Photoredox Catalysis and Elect...mentioning

confidence: 99%

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

2021

View full text Add to dashboard Cite

show abstract

“…The structure of compound 2f was confirmed using an X-ray diffraction study (Supplementary Material (Figures S19 and S20) and Figure 2). Given all the above results and taking into consideration the data on electrocatalytic reactions mediated by iodides [46][47][48] The evolution of hydrogen was the cathodic process, which was accompanied by methoxide anion generation. The formation of iodine was an anodic process and the corresponding iodine color was observed at the anode when the electrolysis was conducted without stirring of the reaction mixture.…”

Section: Resultsmentioning

confidence: 93%

Efficient Electrocatalytic Approach to Spiro[Furo[3,2-b]pyran-2,5′-pyrimidine] Scaffold as Inhibitor of Aldose Reductase

et al. 2021

Self Cite

View full text Add to dashboard Cite

A continuously growing interest in convenient and ‘green’ reaction techniques encourages organic chemists to elaborate on new synthetic methodologies. Nowadays, organic electrochemistry is a new useful method with important synthetic and ecological advantages. The employment of an electrocatalytic methodology in cascade reactions is very promising because it provides the combination of the synthetic virtues of the cascade strategy with the ecological benefits and convenience of electrocatalytic procedures. In this research, a new type of the electrocatalytic cascade transformation was found: the electrochemical cyclization of 1,3-dimethyl-5-[[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl](aryl)methyl]pyrimidine-2,4,6(1H,3H,5H)-triones was carried out in alcohols in an undivided cell in the presence of sodium halides with the selective formation of spiro[furo[3,2-b]pyran-2,5′-pyrimidines] in 59-95% yields. This new electrocatalytic process is a selective, facile, and efficient way to create spiro[furo[3,2-b]pyran-2,5′-pyrimidines], which are pharmacologically active heterocyclic systems with different biomedical applications. Spiro[furo[3,2-b]pyran-2,5′-pyrimidines] were found to occupy the binding pocket of aldose reductase and inhibit it. The values of the binding energy and Lead Finder’s Virtual Screening scoring function showed that the formation of protein–ligand complexes was favorable. The synthesized compounds are promising for the inhibition of aldose reductase. This makes them interesting for study in the treatment of diabetes or similar diseases.

show abstract

“…The best-known electrocatalytic methods for the synthesis of substituted cyclopropanes are as follows: the oxidative cyclization of CH acids; 38 ± 42 cyclotrimerization of CH acids; 43,44 transformations of CH acids and activated alkenes; 47 ± 57 transformations of CH acids and carbonyl compounds; 58 ± 60 multicomponent synthesis of cyclopropanes via electrocatalytic transformation of two different CH acids and a carbonyl compound. 61,62 The electrolysis of organic compounds in an undivided cell without control over the electrode potential in the presence of alkali metal halides as the mediators combines the advantages of electrochemical and chemical processes.…”

Section: Discussionmentioning

confidence: 99%

Electrochemical synthesis of cyclopropanes

Elinson¹,

Dorofeeva²,

Vereshchagin³

et al. 2015

Russ. Chem. Rev.

View full text Add to dashboard Cite

Electrochemical Cyclotrimerization of Cyanoacetic Ester into trans-1,2,3-Tricyanocyclopropane-1,2,3-Tricarboxylate

Cited by 23 publications

References 2 publications

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

Efficient Electrocatalytic Approach to Spiro[Furo[3,2-b]pyran-2,5′-pyrimidine] Scaffold as Inhibitor of Aldose Reductase

Electrochemical synthesis of cyclopropanes

Contact Info

Product

Resources

About