N,N-bis(quinonyl)amines; synthesis and X-ray structure

Bittner, Shmuel; Meenakshi, C.; Temtsin, Galina

doi:10.1016/s0040-4020(01)00717-7

Cited by 40 publications

(25 citation statements)

References 17 publications

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“…3 1,2-Benzoquinone derivatives have been less extensively studied than the 1,4-benzoquinone derivatives because they are more difficult to prepare. 2,4,5 The importance of amino derivatives of quinones has encouraged us to study 6 and synthesize 7 a number of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Electro-organic synthesis of dibenzylaminodioxocyclohexa-dienecarboxylic acids

Nematollahi¹,

Hesari²,

Davarani³

2006

Arkivoc

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Electrochemical oxidation of dihydroxybenzoic acids 1a-c has been studied in the presence of dibenzylamine (3) as nucleophile in water/acetonitrile (90:10) solution using cyclic voltammetry and controlled-potential coulometry. The quinones 2a-c derived from dihydroxybenzoic acids participate in Michael addition reactions with dibenzylamine (3), and via ECE mechanism convert to the corresponding (dibenzylamino)dioxocyclohexadienecarboxylic acids 5a-c.

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Section: Introductionmentioning

confidence: 99%

Electro-organic synthesis of dibenzylaminodioxocyclohexa-dienecarboxylic acids

Nematollahi¹,

Hesari²,

Davarani³

2006

Arkivoc

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“…4) On the other hand, in recent years, medicinal properties of benzofuran derivatives have been investigated widely and were shown to be effective as antitumor, 5) anti-depressant, 6) antifungal, 7) anti-hypertensive, and cytotoxic. 8) They are also potent and selective oxytocin antagonists, 9) PDE5 inhibitor for treatment of erectile dysfunction, 10) and H 3 receptor antagonists.…”

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confidence: 99%

Mechanistic Study of Electrochemical Oxidation of 2,5-Dihydroxybenzoic Acid and 3,4-Dihydroxybenzaldehyde in the Presence of 3-Hydroxy-1H-phenalene-1-one

Nematollahi

Amani

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Quinones are of considerable interest because many drugs such as doxorubicin, daunurobicin and mitomycin C in cancer chemotherapy contain quinones, 1) whereas various other quinones have found use in industry.2) Some of them also exhibit antitumor and antimalarial activities 3) and many of them are also involved in enzyme inhibition and DNA cross-linking.4) On the other hand, in recent years, medicinal properties of benzofuran derivatives have been investigated widely and were shown to be effective as antitumor, 5) anti-depressant, 6) antifungal, 7) anti-hypertensive, and cytotoxic. 8) They are also potent and selective oxytocin antagonists, 9) PDE5 inhibitor for treatment of erectile dysfunction, 10) and H 3 receptor antagonists.11) In order to synthesise new quinone derivatives we studied the electrochemical oxidation of benzenediols in the presence of a variety of nucleophiles.12,13) Also, in order to synthesise benzofuran derivatives we investigated the electrochemical oxidation of catechols in the presence of b-diketones such as acetylacetone, 14) dimedone, 15) and dibenzoylmethane. 16) In this connection, the electrochemical oxidation of hydroquinones and catechols in the presence of 3-hydroxy-1H-phenalene-1-one (3) as a nucleophile has been recently reported by us (Chart 1). 17)In the present paper, we describe the preparation of the new polycyclic quinone derivative 6a and the new polycyclic benzofuran derivative 8b using electrooxidation of 2,5-dihydroxybenzoic acid (1a) and 3,4-dihydroxybenzaldehyde (1b) in the presence of 3-hydroxy-1H-phenalene-1-one (3) as a nucleophile via ECE and ECEC electrochemical mechanisms respectively. Results and DiscussionElectrochemical Study of 2,5 Dihydroxybenzoic Acid Cyclic voltammogram of a 0.5 mM of 2,5-dihydroxybenzoic acid (1a) in water/acetonitrile (80/20) solution containing 0.1 M acetate buffer (pHϭ5.5) is shown in Fig. 1 curve a. As can be seen, one anodic (A 1 ) and its corresponding cathodic peak (C 1 ) was obtained, which correspond to the transformation of 2,5-dihydroxybenzoic acid (1a) to the related p-benzoquinone 2a and vice versa within a quasi-reversible twoelectron process. A peak current ratio (I pA1 /I pC1 ) of nearly unity in the cyclic voltammogram can be considered as a criterion for a stable benzoquinone produced at the surface of electrode under the experimental conditions. In other words, any side reactions such as hydroxylation and/or dimerization reactions are too slow to be observed at the time scale of cyclic voltammetry.17) The oxidation of 2,5-dihydroxybenzoic acid (1a) in the presence of 3 as a nucleophile was studied in some detail. Figure 1 (curve b) shows the cyclic voltammogram obtained for a 0.5 mM solution of 1a in the presence of 0.5 mM 3. The voltammogram exhibits one anodic peak A 1 and two cathodic peaks (C 1 and C 0 ). The second cycle in the cyclic voltammogram (Fig. 1, curve c) shows that, parallel to the decrease in current of A 1 and the shift of its potential in a positive direction, a new anodic peak The mechanism of th...

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“…10,11,28,29 In this study, from the reactions of p-chloranil with 2c, mixture of 2c with 3, 2d and 2e the compounds 4c, 10 7, 12 4d 10 and 4e 10 which have been published previously were respectively synthesized, but their spectroscopic properties weren't investigated intensely before. In addition, from the reactions of 1 with 2a-e and mixture of 2c with 3, in ethanol in the presence of Na2CO3, 4a-b, 5a-e, 6 and the reaction of 1 with 2a-e in methanol in the presence of Na 2 CO 3 , 4a-b and 8a-e were respectively synthesized.…”

Section: Resultsmentioning

confidence: 99%

The Synthesis of Novel Mono(alkoxy)-, Tris(thio)- and Tetrakis(thio)-Substituted Quinones from the Reactions of p-Chloranil with Various S-Nucleophiles

2009

Bulletin of the Korean Chemical Society

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The tetrakis(thio)-substituted-1,4-benzoquinone products 4a-e, 6, 7, and the mono(alkoxy)-tris(thio)-substituted-1,4-benzoquinone products 5a-e and 8a-e were synthesized from the reactions of p-chloranil with some thiols and mixture of two different thiol compounds in alcohol in the presence of Na2CO3 at room temperature. The structures of the novel S,S,S,S-and S,S,S,O-substituted products, which were obtained by the reactions of p-chloranil as a starting compound with n-propanethiol, n-pentanethiol, n-decanethiol, n-dodecanethiol, 2-methyl-2-propanethiol, and mixture of n-decanethiol and n-cyclohexanethiol as S-nucleophiles, were characterized by spectroscopic methods.

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N,N-bis(quinonyl)amines; synthesis and X-ray structure

Cited by 40 publications

References 17 publications

Electro-organic synthesis of dibenzylaminodioxocyclohexa-dienecarboxylic acids

Electro-organic synthesis of dibenzylaminodioxocyclohexa-dienecarboxylic acids

Mechanistic Study of Electrochemical Oxidation of 2,5-Dihydroxybenzoic Acid and 3,4-Dihydroxybenzaldehyde in the Presence of 3-Hydroxy-1H-phenalene-1-one

The Synthesis of Novel Mono(alkoxy)-, Tris(thio)- and Tetrakis(thio)-Substituted Quinones from the Reactions of p-Chloranil with Various S-Nucleophiles

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