72054-83-2

Upstream product

• 60736-94-9 2-Methyl-1,1,4,4-tetramethoxy-2,5-cyclohexadiene 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 108-39-4 3-methyl-phenol 
• 67-56-1 methanol 
• 14786-82-4 4-hydroxy-2-methylanisole 

Downstream Products

• 78176-81-5 4-Hydroxy-1-methoxy-2-methyl-9,10-anthrachinon 
• 132604-82-1 4,4-Dimethoxy-3-methyl-cyclohex-2-enone 
• 1326704-92-0 2,3-dihydro-5-methoxy-6-methyl-2-phenylbenzofuran 
• 1600530-27-5 2-chloro-4-methoxy-5-methylphenol 
• 1431793-56-4 C₁₇H₂₀O₅ 
• 1391994-13-0 C₂₁H₂₃NO₇ 
• 1391994-09-4 C₁₃H₁₅NO₄ 

Relevant academic research and scientific papers

Coupling of Quinone Monoacetals with Vinyl Ethers Effected by Tetrabutylammonium Triflate: Regiocontrolled Synthesis of 2-Oxygenated Dihydrobenzofurans

The synthesis of 2-oxygenated dihydrobenzofurans involving the [3 + 2] coupling of quinone monoacetals with vinyl ethers has been realized by tetrabutylammonium triflate catalysis. The reaction involves a new activation method of the acetal moiety in quinone monoacetals under acid-free conditions affording the highly oxygenated dihydrobenzofurans. This new activation mode was achieved by using the triflate anion catalyst for stabilization of the highly reactive cationic intermediate.

Direct synthesis of anilines and nitrosobenzenes from phenols

A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.

Efficient Coupling Reaction of Quinone Monoacetal with Phenols Leading to Phenol Biaryls

A simple and efficient synthesis of phenol biaryls by the cross-couplings of quinone monoacetals (QMAs) and phenols is reported. The Br?nsted acid catalytic system in 1,1,1,3,3,3-hexafluoro-2-propanol was found to be particularly efficient for this transformation. This reaction can be extended to the synthesis of various phenol biaryls, including sterically hindered biaryls, with yields ranging from 58 to 90 % under mild reaction conditions and in a highly regiospecific manner.

Synthesis of (+)-Antroquinonol and Analogues by Using Enantioselective Michael Reactions of Benzoquinone Monoketals

(+)-Antroquinonol is an anticancer agent that was first isolated from the rare mushroom Antrodia cinnamomea, which is indigenous to Taiwan. In this study, (+)-antroquinonol is synthesized from benzoquinone monoketals by using an enantioselective Michael r

Lewis acid catalyzed [3+2] coupling of indoles with quinone monoacetals or quinone imine ketal

The one-pot synthesis of benzofuroindolines and tetrahydroindolo[2,3-b] indoles was accomplished through a mild and concise [3+2] coupling of indoles and quinone monoacetals or quinone imine ketal promoted by a Lewis acid. A wide variety of benzofuroindolines and tetrahydroindolo[2,3-b]indoles were prepared in moderate to good yields. Copyright

Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N′-dimethylhydrazine dihydrochloride

An unexpected nucleophilic chlorination of a quinone monoketal while carrying out a pyrazolidine synthesis has led to a general preparation of multisubstituted phenols. The products are obtained in good to high yields under mild conditions. The bridged pyrazolidines that were the original targets are obtained in the presence of a protic solvent. This journal is the Partner Organisations 2014.

Br?nsted acid-controlled [3 + 2] coupling reaction of quinone monoacetals with alkene nucleophiles: A catalytic system of perfluorinated acids and hydrogen bond donor for the construction of benzofurans

We have developed an efficient Br?nsted acid-controlled strategy for the [3 + 2] coupling reaction of quinone monoacetals (QMAs) with nucleophilic alkenes, which is triggered by the particular use of a specific acid promoter, perfluorinated acid, and a solvent, fluoroalcohol. This new coupling reaction smoothly proceeded with high regiospecificity in regard with QMAs for introducing π-nucleophiles to only the carbon α to the carbonyl group, thereby providing diverse dihydrobenzofurans and derivatives with high yields, up to quantitative, under mild conditions in short reaction times. The choice of Br?nsted acid enabled us to avoid hydrolysis of the QMAs, which gives quinones, and the formation of discrete cationic species from the QMAs. Notably, further investigations in this study with regard to the acid have led to the findings that the originally stoichiometrically used acid could be reduced to a catalytic amount of 5 mol % loading or less and that the stoichiometry of the alkenes could be significantly improved down to only 1.2 equiv. The facts that only a minimal loading (5 mol %) of perfluoroterephthalic acid is required, readily available substrates can be used, and the regioselectivity can be controlled by the acid used make this coupling reaction very fascinating from a practical viewpoint.

Double hetero-Michael addition of N -substituted hydroxylamines to quinone monoketals: Synthesis of bridged isoxazolidines

A general synthesis of bridged isoxazolidines from a double hetero-Michael addition of N-substituted hydroxylamines to quinone monoketals has been developed. The different addition order of N-benzylhydroxylamine and N-Boc hydroxylamine is also discussed.

A variation of the Fischer indolization involving condensation of quinone monoketals and aliphatic hydrazines

A new twist: A one-pot nitrous acid free, diazonium-free, and transition-metal-free variation of the Fischer indole synthesis has been developed. Condensation of quinone monoketals and aliphatic hydrazine hydrochlorides afforded indoles via intermediate alkylaryldiazenes. This method will complement the classical Fischer indole synthesis by providing indoles in two steps from widely available phenols under mild conditions. Copyright

Efficient synthesis of oxygenated terphenyls and other oligomers: Sequential arylation reactions through phenol oxidation-rearomatization

One by one: Starting from simple phenols, a diverse series of oxygenated terphenyl compounds can be prepared in a concise and practical manner using sequential arylation reactions involving phenol oxidation/rearomatization and quinone monoacetal intermediates (see scheme). Many of the terphenyl products can be used for preparing well-defined oligomers and, furthermore, contain valuable functional groups that can be transformed for further diversification. Copyright