Electro-organic synthesis of dibenzylaminodioxocyclohexa-dienecarboxylic acids

Nematollahi, Davood; Hesari, Mehdi; Davarani, Sayed Saied Hosseiny

doi:10.3998/ark.5550190.0007.a16

Cited by 5 publications

(4 citation statements)

References 5 publications

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“…These results show that nucleophile adds to the reaction site with less negative charge, which is in agreement with the previously published data on the structure of final products. 26,[29][30][31][32][33][34][35] It should be expressed that similar data were obtained using NBO analysis and BP86 level of theory. The results confirm that, in these cases, kinetic effects prevent formation of the thermodynamically preferred product.…”

Section: -2esupporting

confidence: 66%

“…However, according to our previously published papers, site C is more suitable, and compound type P 3 is introduced as the final product of the reaction of p-benzoquinone 6b with various nucleophiles (Scheme 7). 14,[29][30][31][32] In addition, the G aq of reaction sites A and B for o-benzoquinone 2d was found to vary in the order B < A. This result shows that site B is a more suitable position for Michael addition of nucleophiles to o-benzoquinones 2d.…”

Section: -2ementioning

confidence: 85%

“…Contrary to these data, however, we showed that the suitable site in o-benzoquinones 2d for these types of reactions is A (Scheme 8). 14,30,[32][33][34][35] According to these data, it can be concluded that final products (7b and 3d) cannot always be produced in the thermodynamically favored direction, and site-selectivity is not affected by G aq . For more studies, using NBO analysis and B3LYP level of theory, the charge of each reaction site for quinones 2a-2d and 6a,6b was calculated (Fig.…”

Section: -2ementioning

confidence: 86%

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Efficient Factors on the Reaction Rate and Site-Selectivity in Sulfonylation of Catechol and Hydroquinone Derivatives: Experimental and Theoretical Studies

Beiginejad

Nematollahi

Varmaghani

et al. 2013

J. Electrochem. Soc.

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Electrochemical oxidation of some catechol (1a-1e) and hydroquinone (5a,5b) derivatives in the presence of arylsulfinic acids has been investigated both experimentally and theoretically to provide insight into the influence of some factors on the chemical reaction rate of electrogenerated benzoquinones with arylsulfinic acids and site-selectivity of the sulfination of some derivatives of catechol and hydroquinone. The results of this work show that the chemical reaction rate between electrogenerated o-benzoquinones and 4-chlorobenzenesulfinic acid is dependent on the substituent group on the catechol ring. The observed homogeneous rate constants (kobs) of benzoquinones with 4-chlorobenzenesulfinic acid were determined using digital simulation of cyclic voltammograms. In this work, the effect of the change of Gibbs free energy of the chemical reaction and charge on the reaction site were also studied in detail. ΔGaq of the Michael addition reactions and charge of each site of reaction of studied species were calculated using 6–311G (p,d) basis set DFT(B3LYP, BP86) levels of theory. The results show that the charge of the reaction site not only dictates the site of reaction but also indicates the value of the homogeneous rate constants (kobs) of the Michael addition reaction.

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Section: -2esupporting

confidence: 66%

Section: -2ementioning

confidence: 85%

Section: -2ementioning

confidence: 86%

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Efficient Factors on the Reaction Rate and Site-Selectivity in Sulfonylation of Catechol and Hydroquinone Derivatives: Experimental and Theoretical Studies

Beiginejad

Nematollahi

Varmaghani

et al. 2013

J. Electrochem. Soc.

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“…5,6 Aminoquinone has been a subject of study for many years because of its potential medicinal values including antituberculars, antimalaria, antibacterials, and antitumor agents. 7 The importance of amino derivatives of quinones has encouraged us [8][9][10][11][12] and other workers 4,7,[13][14][15] to study and synthesize a number of these compounds. In this work, the electrochemical oxidation of 4-tert-butylcatechol was studied in the presence of some benzenamines as possible nucleophiles.…”

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confidence: 99%

Electrochemical Synthesis of Aminoquinones through Oxidative Coupling of 4-tert-Butylcatechol and Benzenamines

Nematollahi

Barnaji

Salehzadeh

et al. 2014

J. Electrochem. Soc.

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The electrochemical oxidation of 4-tert-butylcatechol in the presence of a series of benzenamines has been evaluated in aqueous solution by means of cyclic voltammetry and controlled-potential coulometry. Results indicate that 4-tert-butylcatechol undergoes a two-electron oxidation at the surface of electrode to 4-tert-butylquinone followed by Michael addition reaction with benzenamine. This study has established the formation of aminoquinones as final products via the ECE mechanism. This procedure would be a good candidate for synthesis of aminoquinones in one-pot process, green conditions and good purity.

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Electrochemical synthesis of new organic compounds based on the oxidation of 1,4-dihydroxybenzene derivatives in the presence of primary and secondary amines

Nematollahi¹,

Hesari²,

Salehzadeh³

et al. 2015

Comptes Rendus. Chimie

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An efficient method for the synthesis of 2-benzyl(4-hydroxyphenyl)amino)-6-(benzylamino)-p-benzoquinone derivatives and 2,5-bis-benzyl(methyl)amino)-p-benzoquinone based on the Michael type reaction is described. The electrochemically generated p-benzoquinone reacted with benzylamine derivatives (primary amines) and N-methylbenzylamine (a secondary amine), respectively, to produce the final products. In this work, some new symmetric and asymmetric p-benzoquinone derivatives are synthesized using green solvents with high yields.

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Electro-organic synthesis of dibenzylaminodioxocyclohexa-dienecarboxylic acids

Cited by 5 publications

References 5 publications

Efficient Factors on the Reaction Rate and Site-Selectivity in Sulfonylation of Catechol and Hydroquinone Derivatives: Experimental and Theoretical Studies

Efficient Factors on the Reaction Rate and Site-Selectivity in Sulfonylation of Catechol and Hydroquinone Derivatives: Experimental and Theoretical Studies

Electrochemical Synthesis of Aminoquinones through Oxidative Coupling of 4-tert-Butylcatechol and Benzenamines

Electrochemical synthesis of new organic compounds based on the oxidation of 1,4-dihydroxybenzene derivatives in the presence of primary and secondary amines

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