Oxidative coupling of quinones and aromatic compounds by palladium(II) acetate

Itahara, Toshio

doi:10.1021/jo00350a023

Cited by 89 publications

(40 citation statements)

References 2 publications

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“…The title compound was prepared as described in literature [1] and recrystallized from dichloromethane-petroleum ether solution at room temperature to give the desired crystals suitable for diffraction experiment.…”

Section: Source Of Materialsmentioning

confidence: 99%

Crystal structure of 2-phenyl-1,4-benzoquinone, C12H8O2

Bai¹,

Chen²,

Liu³

2011

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Source Of Materialsmentioning

confidence: 99%

Crystal structure of 2-phenyl-1,4-benzoquinone, C12H8O2

Bai¹,

Chen²,

Liu³

2011

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Examples of reactions between heteroarenes and olefins in the presence of palladium acetate are well known [36]. This method was used for the production of substituted 1,4-naphthoquinones 13a-f [11], 13g [37], and 13h [38]. According to data in [11], oxidative coupling between naphthoquinone and thiophene or furan does not occur under these conditions.…”

Section: Oxidative Coupling Of 14-naphthoquinones With Heteroarenes mentioning

confidence: 99%

Methods for the Synthesis of Heteroaryl-substituted 1,4-Benzo- and 1,4-Naphthoquinones. (Review)

Batenko¹,

Karlivans²,

Valters³

2005

Chem Heterocycl Compd

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Methods for the synthesis of heteroaryl-substituted 1,4-benzo-and 1,4-naphthoquinones with a C-C bond between the heterocycle and quinone fragments are reviewed.Benzoquinones and their derivatives are widely used in organic synthesis as synthons and reagents [1,2]. They are used as electron-accepting components for the production of charge-transfer complexes and radicalion salts [3,4]. Derivatives of benzoquinones, isolated from natural sources, are subunits in many biological processes, such as electron transport, the photosynthesis of plants, the coagulation of blood, and cell respiration [1, 2, 5]. Reviews have been published on the synthesis of hydroxyquinones [6] and 1,4-benzoquinones condensed with heterocycles [7,8], but methods for the synthesis of heteroaryl derivatives of 1,4-benzoquinones and 1,4-naphthoquinones where the fragments of the heterocycle and the quinone are linked by a C-C bond have not so far been reviewed. Heteroaryl-substituted benzoquinones have demonstrated anticancer [9-11], antifungal, and antibacterial characteristics [11] and antidiabetic activity [12]. The present review is devoted to the analysis and classification of methods for the production of these compounds. Methods for the synthesis of heteroaryl derivatives of quinones can be divided into three groups: The formation of a C-C bond between the quinone and the heterocycle, construction of the heterocycle on the basis of the quinone, and construction of the quinone on the basis of the heterocycle.

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“…These derivatives 15-41 were synthesized following standard procedures starting from either naphthalene-1,4-dione 7 or 2-bromonaphthalene 8. 26 The oxidative coupling of naphthalene-1,4-dione 7 with 2-substituted heterocycles in acetic acid and stoichiometric amounts of palladium acetate under reflux conditions gave the corresponding 2-heteroaryl-substituted naphthalene-1,4-diones 15-20, 29, 30, 31, and 33-41 (Scheme 1). Compounds 21-24 and 32 were prepared via Heck coupling of 2-bromonaphthalene 8 with different acrylic esters to give 2-substituted naphthalene esters 9-13 and followed by their oxidation with periodic acid and chromium trioxide (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of substituted naphthoquinone derivatives as potent antimycobacterial agents

Mital¹,

Negi²,

Ramachandran³

2008

Arkivoc

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In the present study, a series of 1,4-naphthoquinone derivatives were synthesized and screened for antitubercular activity against Mycobacterium tuberculosis H 37 Rv strain by the broth microdilution assay method. The in vitro antitubercular activity data of the tested compounds against M. tuberculosis strain H 37 Rv showed moderate to good activity against bacteria compared to reference drugs. The most effective compounds of the series are 26, 28, 29, 34 and 36 with IC 50 values ranging from 3.9 -0.3 µg/mL. The objective of our study is to generate new leads that operate through a different mode of action and to optimize their structure to display potent efficacy.

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Oxidative coupling of quinones and aromatic compounds by palladium(II) acetate

Cited by 89 publications

References 2 publications

Crystal structure of 2-phenyl-1,4-benzoquinone, C12H8O2

Crystal structure of 2-phenyl-1,4-benzoquinone, C12H8O2

Methods for the Synthesis of Heteroaryl-substituted 1,4-Benzo- and 1,4-Naphthoquinones. (Review)

Synthesis and biological evaluation of substituted naphthoquinone derivatives as potent antimycobacterial agents

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