The synthesis of quinones

Owton, W. Martin

doi:10.1039/a707426c

Cited by 52 publications

(22 citation statements)

References 85 publications

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“…Hosttetman and co-workers 54 isolated two novel benzoquinones heliotropinones A (22) and B (23), from the aerial parts of Heliotropium ovalifolium. These two quinones demonstrated antifungal activities against Cladosporium cucumerinum and Candida albicans as well as antibacterial activity against Bacillus subtilis.…”

Section: Introductionmentioning

confidence: 99%

“…[14][15][16][17][18][19][20] Coordination chemistry of quinones is also quite rich from the perspective of designing magnetic materials 21 and understanding photophysical properties. 22 The studies of quinonoid compounds have focused on a broad spectrum of topics viz occurrence in nature, 2 syntheses, 23 cycloaddition reactions, 24 photochemistry and pulse radiolysis, 1,25,26 computational chemistry, etc. 27 The copiousness of articles describing the aforementioned multi-functional aspects serves as a grand testimonial to the contemporary interest in quinone chemistry.…”

Section: Introductionmentioning

confidence: 99%

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Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

169

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As 1,4-benzoquinonas são encontradas em toda a natureza, podendo ser sintetizadas por diversas estratégias. Esta revisão apresenta os desenvolvimentos recentes das metodologias de síntese, das reações de ciclo adição, da química computacional e dos estudos de pulso radiolítico. Destaca ainda a sua significância química e biológica e de seus compostos derivados.1,4-Benzoquinones are ubiquitous in nature and can be synthesized by diverse strategies. Recent developments on their synthetic methodologies, cycloaddition reactions, computational chemistry and pulse radiolytic studies are reported in this review. Their chemical and biological significance as well as their derivates' are also covered.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

169

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“…37 Deprotection of such 1,4-dimethoxybenzene is typically achieved by cerium ammonium nitrate (CAN) mediated oxidation. [38][39] (IV) In a similar manner (±)-plumbazeylanone (54), a trimer of naphthoquinone, was achieved by exhaustive demethylation of ether 53 followed by air oxidation in 65% yield (Scheme 3D). 40 (V) Resveratrol (56b) and its derivatives such as oxyresveratrol (56c) and piceatannol (56d) were obtained by exhaustive deprotection of related phenolic methyl ethers (55).…”

Section: Exhaustive Demethylationmentioning

confidence: 99%

“…32 The method was applied in syntheses of four coumarin analogues (39~42) applicable to organic light emitting displays as fluorescent dyes. Key intermediate 3-hydroxytriphenylamine (38) was prepared in a two-step procedure: Ulmann coupling of iodobenzene and m-anisidine (36) furnished anisole 37; demethylation of 37 with AlI 3 afforded 38 in 93% yield (Scheme 2F). …”

Section: Solvent Effectsmentioning

confidence: 99%

Application of aluminum triiodide in organic synthesis

Tian¹,

Sang²

2015

Arkivoc

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The multifaceted reactivity of aluminum triiodide (AlI 3 ) is reviewed. The oxophilic character of the Lewis acid enables the formation of coordination complexes with esters, ethers, oxiranes, diols, Noxides, and sulfoxides that decompose spontaneously to afford acids, alcohols and olefins via ester and ether cleavage, deoxygenation of oxiranes, and deoxydehydration of diols, respectively. As an iodide ion source and hydrogen iodide precursor, the reagent allows iodination and reduction of Noxides, sulfoxides and azides as well as hydroiodination of alkenes and alkynes. Aluminum enolates, generated by treatment of -haloketones with AlI 3 , provide accesses to -hydroxy ketones, 1,5-diones, and β-iodo Morita-Baylis-Hillman esters.

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“…1 Synthetically, the para-benzoquinone structural unit is an excellent dienophile for the Diels-Alder reaction, among other relevant reactions. 1 The usual and obvious manner to prepare parabenzoquinones 1,14,15 is from the corresponding parahydroquinones, which is however rather limited due to the lack of a wide range of commercially or synthetically available substrates. As a second choice, the simple monophenol is an ideal substrate due to the ready availability of an extremely wide range of such compounds.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of mono-phenols to para-benzoquinones: a comparative study

Uliana¹,

Vieira²,

Donatoni³

et al. 2008

J. Braz. Chem. Soc.

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A oxidação de mono-fenóis à para-benzoquinonas é assunto de interesse contínuo devido à existência de inúmeros produtos naturais contendo esta unidade estrutural. As para-benzoquinonas possuem reatividade química importante como agentes oxidantes e como dienófilos na reação de Diels-Alder. Usualmente nós preparamos as para-benzoquinonas pela reação de oxidação dos respectivos mono-fenóis com oxigênio molecular e catalisada por [Co II (salen)]. Porém, foi necessário estudar estas oxidações utilizando-se outros oxidantes. Nós apresentamos aqui nossos resultados sobre esta importante reação de oxidação com uma variedade de oxidantes, utilizando onze mono-fenóis como substratos. Os oxidantes utilizados foram cobalto, níquel, cobre e vanádio derivados com alguns ligantes do tipo salen. Também foram estudados peróxido de hidrogênio, OXONE®, dimetil dioxirano e ácido iodoxibenzóico.The oxidation of mono-phenols to para-benzoquinones is of continuing interest due to the existence of numerous natural products containing this structural unit. The chemical reactivity of para-benzoquinones is also noteworthy, as oxidants and dienophiles in the Diels-Alder reaction. We have used for quite some time now, molecular oxygen and catalysis with [Co II (salen)] as the oxidation procedure, but felt the need for other oxidants and conditions to be of use with different phenol substrates. We now present our results on this important oxidation with a variety of oxidants, using eleven mono-phenols as substrates. The oxidants tested are cobalt, nickel, copper and vanadyl metals, with a selection of different salen type ligands. Completing this study we also investigated the use of hydrogen peroxide, OXONE®, dimethyl dioxirane and iodoxybenzoic acid. Keywords: oxidation, alkyl-substituted phenols, para-benzoquinones IntroductionNatural products frequently occur containing the parabenzoquinone sub-structural unit within the global structure, as can be exemplified by vitamins K 1 and K 2 , co-enzyme Q (ubiquinone), 1 and in many terpenes and alkaloids. 2 These natural products 3-13 are associated with important biological properties, such as cardiovascular, anti-tumour, antibacterial, anti-germination and anti-protozoan among others. There is no doubt that the para-benzoquinone nucleus is an important charge transfer receptor and easily undergoes nucleophilic addition reactions. 1 The redox relation with para-hydroquinones (para-quinols) is of importance in biological activity, and also makes many simple para-benzoquinones excellent oxidizing agents. 1 Synthetically, the para-benzoquinone structural unit is an excellent dienophile for the Diels-Alder reaction, among other relevant reactions. 1 The usual and obvious manner to prepare parabenzoquinones 1,14,15 is from the corresponding parahydroquinones, which is however rather limited due to the lack of a wide range of commercially or synthetically available substrates. As a second choice, the simple monophenol is an ideal substrate due to the ready availability of an extremely wide range of...

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The synthesis of quinones

Cited by 52 publications

References 85 publications

Recent advances in 1,4-benzoquinone chemistry

Recent advances in 1,4-benzoquinone chemistry

Application of aluminum triiodide in organic synthesis

Oxidation of mono-phenols to para-benzoquinones: a comparative study

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