Facile Oxidation of Fused 1,4-Dimethoxybenzenes to 1,4-Quinones Using NBS:  Fine-Tuned Control over Bromination and Oxidation Reactions

Kim, Dong Wook; Choi, Han Young; Lee, Kee‐Jung; Yoon, Dae

doi:10.1021/ol006952r

Cited by 47 publications

(24 citation statements)

References 31 publications

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“…Quinoline-5,8-diones can be synthesized in high yield (>90%) by oxidative demethylation of 5,8-dimethoxyquinolines, 19 which can be prepared from 2,5-dimethoxyaniline derivatives with the help of a modified Skraup reaction, although in poor yield (20%). 20 However, once again, the desired aniline derivatives are not commercially available.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents

et al. 2012

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Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents

et al. 2012

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“…Unfortunately, benzodithiophene-4,8-dione 9 was obtained in this case, presumably because the NBS promoted oxidative dealkylation. 32 Therefore, the bromination reaction was performed with the proton abstraction reaction using n-butyl lithium and then treated with 1,2-dibromoethane to afford monobrominated products 4 with a 67% yield (Scheme 2). We then studied the polymerization reaction of bromide 1a and triflate 1b that resulted in the head-to-tail type poly(thienylenephenylene).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of π-conjugated poly(thienylenearylene)s with nickel-catalyzed C–H functionalization polycondensation

Tamba

Okubo

Sugie

et al. 2012

Polym J

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p-Conjugated polymers are synthesized by C-H and C-X polycondensation of 2-(4-haloaryl)thiophene monomers with a nickel catalyst, and the Knochel-Hauser base (TMPMgCl . LiCl (chloromagnesium 2,2,6,6-tetramethylpiperidide lithium chloride salt)). The C-H functionalization polycondensation reaction of a monobrominated monomer undergoes dehydrobrominative polymerization with an equimolar amount of TMPMgCl . LiCl and a catalytic amount of NiCl 2 dppp to produce poly(2,5-thienylene-1,4-phenylene) and poly(2,5-thienylenepyridine-2,5-diyl) with reasonable yields. Polycondensation with triflate as a leaving group proceeds under similar conditions to produce poly(thienylenephenylene) with an excellent yield. Poly(benzodithiophene) was also obtained from the reaction of the corresponding monobrominated benzodithiophene in the presence of a nickel-catalyst-bearing N-heterocyclic carbene as a ligand.

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“…7) uses NBS and catalytic quantities of sulfuric acid at 20°C, stirred for 5 min, and produces quantitative yields. When the acid catalyst is omitted, the product is a Br-derivative (Kim et al, 2001).…”

Section: Synthetic Methodsmentioning

confidence: 99%

Quinoid systems in chemistry and pharmacology

et al. 2015

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In this paper, we present a brief review of quinoid systems, focusing on their chemical synthesis over the last decade. We address not only major methods of synthesizing quinoids, but also their involvement in biological processes. We highlight their medical relevance and versatility, including antitumor, antiretroviral, or antihypertensive agents, properties determined by their various patterns of substitution. Graphical AbstractKeywords Quinone Á Synthesis Á Cytotoxicity Á Natural products Á Pharmacology Á Redox Abbreviations 3a-HSD 3a-Hydroxysteroid dehydrogenase AIDS Acquired Immune Deficiency Syndrome AlnA Alnumycin A AlnB Alnumycin B BAQ Benzanthracene quinone (7,12-benzo[a] anthraquinone) BPQ Benzo[a]pyrene-7,8-dione CAN Ceric ammonium nitrate CC 50 50 % Cytotoxic concentration CDC25 Cell division cycle phosphatases Cyt Ferricytochrome d-A 2 0 -Deoxyadenosine DBU 1,8-Diazabicyclo[5.4.0]undec-7-ene DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone d-G, d-Guo 2'-Deoxyguanosine DMF N,N-dimethylformamide DMP Dess-Martin periodinane DMSO

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Facile Oxidation of Fused 1,4-Dimethoxybenzenes to 1,4-Quinones Using NBS: Fine-Tuned Control over Bromination and Oxidation Reactions

Cited by 47 publications

References 31 publications

Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents

Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents

Synthesis of π-conjugated poly(thienylenearylene)s with nickel-catalyzed C–H functionalization polycondensation

Quinoid systems in chemistry and pharmacology

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