- Palladium-catalyzed direct C-H functionalization of benzoquinone
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A direct Pd-catalyzed C-H functionalization of benzoquinone (BQ) can be controlled to give either mono- or disubstituted BQ, including the installation of two different groups in a one-pot procedure. BQ can now be directly functionalized with aryl, heteroaryl, cycloalkyl, and cyclo-alkene groups and, moreover, the reaction is conducted in environmentally benign water or acetone as solvents.
- Walker, Sarah E.,Jordan-Hore, James A.,Johnson, David G.,MacGregor, Stuart A.,Lee, Ai-Lan
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supporting information
p. 13876 - 13879
(2015/02/05)
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- Tandem oxidation-oxidative C-H/C-H cross-coupling: Synthesis of arylquinones from hydroquinones
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A concise and efficient approach to arylquinones from widely available hydroquinones has been developed through a tandem reaction involving the oxidation of hydroquinones and subsequent oxidative C-H/C-H cross-coupling of the resulting quinones with arenes.
- Zhang, Shuai,Song, Feijie,Zhao, Dongbing,You, Jingsong
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supporting information
p. 4558 - 4560
(2013/06/04)
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- Synthesis and evaluation of arylquinones as BACE1 inhibitors, β-amyloid peptide aggregation inhibitors, and destabilizers of preformed β-amyloid fibrils
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BACE1 activity, inhibition of Aβ aggregation, and disaggregation of preformed Aβ fibrils constitute the three major targets in the development of small-molecule lipophilic new drugs for the treatment of Alzheimer's disease (AD). Quinones are widely distributed among natural products and possess relevant and varied biological activities including antitumor and antibiotic, inhibition of HIV-1 reverse transcriptase, antidiabetic, or COX-inhibition, among others. We report herein the interaction of several arylquinones and their derivatives with the amyloidogenic pathway of the amyloid precursor protein processing. Our studies put forward that these compounds are promising candidates in the development of new drugs which are effective simultaneously towards the three major targets of AD.
- Ortega, Andrea,Rincón, ángela,Jiménez-Aliaga, Karim L.,Bermejo-Bescós, Paloma,Martín-Aragón, Sagrario,Molina, María Teresa,Csák?, Aurelio G.
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supporting information; experimental part
p. 2183 - 2187
(2011/05/15)
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- Studies on the Meerwein Arylation-Based Preparation of 2,3-Diarylbenzene-1,4-diones and Its Theoretical Interpretation
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Title compounds possessing a variety of substituents are systematically prepared by means of Meerwein arylation of benzene-1,4-dione. Synthetic aspects and their MNDO calculation-based interpretation are described.
- Takahashi, Ichiro,Muramatsu, Osamu,Fukuhara, Jun,Hosokawa, Yoshinao,Takeyama, Naohiko,et al.
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p. 465 - 468
(2007/10/02)
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- Oxidative Coupling of Quinones and Aromatic Compounds by Palladium(II) Acetate
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The oxidation of 1,4-benzoquinone, 2-phenyl-1,4-benzoquinone, 1,4-naphthoquinone, and 1,2-naphthoquinone by palladium(II) acetate in acetic acid containing arenes gave the corresponding aryl-sustituted quinones.Treatment of 1,4-naphthoquinone with aromatic heterocycles such as furfural, 2-acetylfuran, methyl 2-furoate, 2-acetylthiophene, 1-(phenylsulfonyl)pyrrole, 1-(phenylsulfonyl)indole, 4-pyrone, and 1-methyl-2-pyridone in the presence of palladium acetate gave the corresponding 2-heteroaryl-substituted 1,4-naphthoquinones.
- Itahara, Toshio
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p. 5546 - 5550
(2007/10/02)
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- Arylation of Quinones with Arenes and Palladium Acetate
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Oxidation of quinones with palladium acetate in acetic acid, which contained arenes, gave arylated quinones.
- Itahara, Toshio
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p. 859 - 860
(2007/10/02)
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- Synthesis of Substituted Quinones. 2,5-Disubstituted 1,4-Benzoquinones
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Synthetic methodology is presented which allows the facile synthesis of 2,5-disubstituted 1,4-benzoquinones.This involves the initial 1,2-addition of an alkynyllithium reagent to one of the carbonyl groups of 2,5-diethoxy- or 2,5-dichloro-3,6-dimethoxy-1,4-benzoquinone.This is followed by an analogous addition of an alkyl-, aryl-, or alkynyllithium to the remaining carbonyl to give a cyclohexa-2,5-diene-1,4-diol derivative.Acid hydrolysis of these adducts results in the 2,5-dialkylated 1,4-benzoquinones.This methodology was employed to prepare 7-chloro-6-methyl-1,2,5,8-tetrahydro-3H-pyrroloindole-5,8-dione (14), a compound having the basic ring systeme of the mitomycin antineoplastic antibiotics.
- Moore, Harold W.,Sing, Yuen-Lung L,Sidhu, Ravinder S.
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p. 5057 - 5064
(2007/10/02)
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