The Polarography of Quinoxaline. II.<sup>1</sup> 6-Substituted Derivatives<sup>2</sup>

Strier, M. P.; Cavagnol, J. C.

doi:10.1021/ja01540a014

Cited by 25 publications

(8 citation statements)

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“…These results are consistent with facilitation of quinoxaline reduction by a positive charge at the reaction site [18]. This is further demonstrated by (Table 4, [19]) and  is the reaction constant [18,20]. Comparison of the data in Tables 1 and 2 demonstrates that the substituent group at R 2 has relatively little effect on reduction potential, presumably due to the distance from the site of reduction.…”

Section: Relationship Between Electrochemical Behavior and Structuresupporting

confidence: 80%

Cyclic Voltammetric Study of Some Anti‐Chagas‐Active 1,4‐Dioxidoquinoxalin‐2‐yl Ketone Derivatives

Pérez‐Silanes¹,

Devarapally²,

Torres³

et al. 2013

Helvetica Chimica Acta

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The electrochemical properties of 24 quinoxaline 1,4-di-N-oxide-2-ketone derivatives with varying degrees of anti-chagas activity were investigated in the aprotic solvent dimethylformamide (DMF) using cyclic voltammetry and first derivative cyclic voltammetry. For this group of compounds, the first reduction in DMF was either reversible or quasireversible and consistent with reduction of the N-oxide functionality to form the radical anion. The second reduction process for these compounds was found to be irreversible under the conditions used. The reduction potentials correlated well with molecular structure. Substitution in the 3-, 6-, and 7-positions of the quinoxaline ring by electron-withdrawing substituents directly affects the ease of reduction and improves the biological activities of these compounds, whereas substitution by electrondonating groups has the opposite effect. The results of this study when combined with previous work into their mechanism of action against chagas disease suggest that charge transfer might play a role in the mechanism of action for these compounds.

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Section: Relationship Between Electrochemical Behavior and Structuresupporting

confidence: 80%

Cyclic Voltammetric Study of Some Anti‐Chagas‐Active 1,4‐Dioxidoquinoxalin‐2‐yl Ketone Derivatives

Pérez‐Silanes¹,

Devarapally²,

Torres³

et al. 2013

Helvetica Chimica Acta

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“…The reduction of quinoxalines in aprotic media produces the radical species [11][12][13][14], and is different from that in protic media [15][16][17][18][19][20][21][22]. For this reason, 98% H 2 SO 4 was used to adjust the solution pH and to act as the proton source of the electrochemical reaction.…”

Section: Methodsmentioning

confidence: 99%

Electrochemical behavior of conjugated quinoxaline derivatives

Wang

Ramaraj

Okajima

et al. 2004

Journal of Electroanalytical Chemistry

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“…Several further series of polarographic data can be added to JaffB's list, namely, the reduction of iodobenzenes (62), the reduction of benzaldehydes and acetophenones (63) the reduction of 6-substituted quinoxalines (225) and the oxidation of p-substituted phenylferrocenes (179). The ionization potentials of free radicals have been suggested (146) as a measure of "absolute Lewis base strength."…”

Section: The Correlation Of Non-reactivity Datamentioning

confidence: 99%