A distal vinyl shift (DVS) through quadruple domino reaction: synthesis of <i>N</i>-vinyl benzoheterocyclic scaffolds

Bakthadoss, Manickam; Mushaf, Mohammad

doi:10.1039/c8ra01478g

Cited by 16 publications

(2 citation statements)

References 54 publications

(21 reference statements)

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“…Anilide, an important building block molecule to produce pyrazolidine-3,5-diones and benzoxazoles which are important heterocyclic motifs appearing in natural products and drugs, − provides a key ring skeleton for many other medicinally relevant compounds. − One of the simple routes to synthesize these compounds was previously reported as the electrochemical N–N bond formation of dianilide by the anodic oxidation of anilide . The electrochemical oxidation pathway in the hexa-fluoroisopropanol (HFIP) solvent was suggested as an ECE mechanism (Scheme ): subsequent single electron transfer (SET) and deprotonation to amidyl radical followed by another SET to the cation.…”

Section: Resultsmentioning

confidence: 99%

Revisiting Thin-Layer Electrochemistry in a Chip-Type Cell for the Study of Electro-organic Reactions

Shin

Kim

et al. 2021

Anal. Chem.

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It is important but challenging to elucidate the electrochemical reaction mechanisms of organic compounds using electroanalytical methods. Particularly, a rapid and straightforward method that provides information on reaction intermediates or other key electrochemical parameters may be useful. In this work, we exploited the advantages of classic thin-layer electrochemistry to develop a thin-layer electroanalysis microchip (TEAM). The TEAM provided better-resolved voltammetric peaks than under semi-infinite diffusion conditions owing to its small height. Importantly, rapid and accurate determination of the number of electrons transferred, n, was enabled by mechanically confining the microliter-scale volume analyte at the electrode, while securing ionic conduction using polyelectrolyte gels. The performance of the TEAM was validated using voltammetry and coulometry of standard redox couples. Utilizing the TEAM, a (spectro)electrochemical analysis of FM 1–43, an organic dye widely used in neuroscience, was successfully performed. Moreover, the TEAM was applied to study the electrochemical oxidation mechanism of pivanilides and alkyltrifluoroborate salts with different substituents and solvents. This work suggests that TEAM is a promising tool to provide invaluable mechanistic information and promote the rational design of electrosynthetic strategies.

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Section: Resultsmentioning

confidence: 99%

Revisiting Thin-Layer Electrochemistry in a Chip-Type Cell for the Study of Electro-organic Reactions

Shin

Kim

et al. 2021

Anal. Chem.

View full text Add to dashboard Cite

show abstract

“…Anilide, an important building block molecule to produce pyrazolidine-3,5-diones and benzoxazoles which are important heterocyclic motifs appearing in natural products and drugs, [47][48][49][50][51][52] provides a key ring skeleton for many other medicinally relevant compounds (Figure 4a). [53][54][55][56][57] One of the simple routes to these compounds was previously reported to be the electrochemical N-N bond formation of dianilide by anodic oxidation of anilide. 58 The electrochemical oxidation pathway in hexafluoroisopropanol (HFIP) solvent was suggested as an ECE mechanism (Figure 4b): subsequent single electron transfer (SET) and deprotonation to amidyl radical followed by another SET to cation.…”

Section: Resultsmentioning

confidence: 99%

Revisiting Thin-Layer Electrochemistry in a Chip-Type Cell for the Study of Electroorganic Reactions

Shin

Kim

et al. 2021

Preprint

View full text Add to dashboard Cite

It is important but challenging to elucidate the electrochemical reaction mechanisms of organic compounds using electroanalytical methods. Particularly, a rapid and straightforward method may be helpful if it can provide information on reaction intermediates or other key electrochemical parameters. In this work, we exploited the advantages of classic thin-layer electrochemistry to develop a thin-layer electroanalysis microchip (TEAM). TEAM provided better resolved voltammetric peaks than under semi-infinite diffusion condition owing to the small height. Importantly, rapid and accurate determination of the number of electrons transferred, n, was enabled by mechanically confining the microliter-scale volume analyte at the electrode, while securing ionic conduction using polyelectrolyte gels. The performance of the TEAM was validated using voltammetry and coulometry of standard redox couples. Utilizing TEAM, a (spectro)electrochemical analysis of FM 1-43, an organic dye widely used in neuroscience, was successfully performed. It was also applied to study the electrochemical oxidation mechanism of pivanilides and alkyltrifluoroborate salts with different substituents and solvents. This work suggests the TEAM as a promising tool to provide invaluable mechanistic information and promote the rational design of electrosynthetic strategies.

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Recent Advances in the Use of 2‐Aminobenzyl Alcohols in the Synthesis of Quinolines, Quinazolines and Other N‐Heterocycles

Doraghi,

Gilaninezhad,

Karimian

et al. 2024

Adv Synth Catal

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N‐Heterocyclic compounds, in particular, quinolines and quinazolines are frequently used in medicinal chemistry. Therefore, the direct and clean synthesis of these valuable scaffolds has been a great interest for many years. 2‐Aminobenzyl alcohols as an alternative reactant instead of unstable and expensive 2‐aminobenzaldehydes can be used in the construction of N‐fused heterocycles including quinolines, quinazolines, oxazines, thiazines, selenazines, imidazoles, diazepines, etc. In this review article, we have discussed recent developments in the use of 2‐aminobenzyl alcohols in the synthesis of diverse heterocycles

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A distal vinyl shift (DVS) through quadruple domino reaction: synthesis of N-vinyl benzoheterocyclic scaffolds

Abstract: An unprecedented Distal Vinyl Shift (DVS) through quadruple domino reaction has been disclosed via the synthesis of N-vinyl benzoheterocyclic scaffolds.

Cited by 16 publications

References 54 publications

Revisiting Thin-Layer Electrochemistry in a Chip-Type Cell for the Study of Electro-organic Reactions

Revisiting Thin-Layer Electrochemistry in a Chip-Type Cell for the Study of Electro-organic Reactions

Revisiting Thin-Layer Electrochemistry in a Chip-Type Cell for the Study of Electroorganic Reactions

Recent Advances in the Use of 2‐Aminobenzyl Alcohols in the Synthesis of Quinolines, Quinazolines and Other N‐Heterocycles

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