1074-12-0Relevant articles and documents
Palladium/benzoquinone-catalyzed electrochemical oxidation of alcohols under anaerobic conditions
Amatore, Christian,Cammoun, Chama,Jutand, Anny
, p. 2173 - 2178 (2007)
Primary and secondary alcohols are oxidized to aldehydes and ketones, respectively, under anaerobic conditions in DMF at 80°C, in the presence of a base and catalytic amounts of Pd(OAc)2 and p-benzoquinone. The latter oxidizes the transient Pd(0) formed in the catalytic cycle to Pd(II) and p-hydroquinone is re-oxidized electrochemically. Georg Thieme Verlag Stuttgart.
Arylacetylenes as two-carbon synthons: Synthesis of eight-membered rings: Via CC bond cleavage
Zhao, Peng,Yu, Xiao-Xiao,Zhou, You,Huang, Chun,Wu, Yan-Dong,Zhu, Yan-Ping,Wu, An-Xin
, p. 12554 - 12557 (2020)
The first synthesis of eight-membered N-containing heterocycles by oxidative bicyclization/ring extension of arylacetylenes and aryl amines has been achieved. This protocol uses arylacetylene as an unusual two-carbon synthon by incorporating the two parts of the cracked CC bond into the final product, which provides a new method for using arylacetylenes as two-carbon synthons and further enriches CC bond cleavage methodology. Moreover, this multi-component reaction can provide diverse fused elegant eight-membered N-heterocycles under mild conditions with wide substrate scopes.
Four-component reaction of α-naphthol, an arylglyoxal, aniline and a dialkyl acetylenedicarboxylate: A Michael addition of enamines to α,β-unsaturated γ-dicarbonyl compounds
Mehrabi, Hossein,Fadaei, Mohadeseh,Zadeh, Ashrafosadat Beheshti
, p. 640 - 642 (2016)
Seven new tetracyclic diesters [dialkyl 1-Anilino-4-Aryl-3-(1-hydroxynaphthalen-2-yl)-4-oxobut-1-ene-1,2-dicarboxylates] have been prepared in good yield by a one-pot four-component reaction between enamine intermediates (as Michael donors) generated from aniline and a dialkyl acetylenedicarboxylate and α,β-unsaturated β-dicarbonyl intermediates (as Michael acceptors) generated fromα-naphthol and an arylglyoxal without using a catalyst in ethanol at reflux conditions.
Regioselective oxidative cross-coupling of benzo[d] imidazo[2,1- b] thiazoles with styrenes: A novel route to C3-dicarbonylation
Shaik, Siddiq Pasha,Sultana, Faria,Ravikumar,Sunkari, Satish,Alarifi, Abdullah,Kamal, Ahmed
, p. 7696 - 7704 (2017)
A novel I2 promoted, highly efficient metal-free and peroxide-free greener domino protocol for the C3-dicarbonylation of benzo[d]imidazo[2,1-b]thiazoles (IBTs) with styrenes has been developed via oxidative cleavage of the C(sp2)-H bond, followed by C3-nucleophilic attack of IBT and oxidation. Interestingly, under these conditions 2-(benzo[d]imidazo[2,1-b]thiazol-2-yl)aniline gave the benzo[4′,5′]thiazolo[2′,3′:2,3]imidazo[4,5-c]quinoline derivative via oxidative cleavage of the C(sp2)-H bond, followed by Pictet-Spengler cyclization and aromatization. This method offers the advantages of broad substrate scope, ecofriendly feature and high atom economy apart from higher yields.
Synthesis of fused pyrroles containing 4-hydroxycoumarins by regioselective metal-free multicomponent reactions
Mishra, Richa,Jana, Asim,Panday, Anoop Kumar,Choudhury, Lokman H.
, p. 3289 - 3302 (2018)
The reaction of arylglyoxals, 4-hydroxycoumarin, and aromatic amines such as 7-amino-2-methylchromone, 6/7-aminoflavone, 7-amino-4-methylcoumarin, 1-amino-9-fluorenone, 1-aminoanthraquinone and aniline derivatives in acetic acid medium under microwave conditions provides the corresponding regioselective fused pyrroles having hydroxycoumarin and aryl substituents. Alternatively, we have developed another method using in situ arylglyoxals from acetophenone derivatives by I2/DMSO promoted C-H oxidation followed by one-pot three component cyclization reactions to provide similar fused pyrroles. Using both the methods a series of novel pyrroles fused with pharmacologically important chromone, flavone, coumarin, fluorenone, and anthraquinone moieties were synthesized under metal-free reaction conditions in good to very good yields within a short reaction time. The structures of the synthesized fused pyrroles have been unambiguously confirmed by spectroscopic techniques, mass analysis and single crystal XRD.
Synthesis and solid-state luminescence of highly-substituted 6-amino-2H-pyran-2-one derivatives
Karpov, Sergey,Kayukov, Yakov,Grigor'ev, Arthur,Nasakin, Oleg,Kayukova, Olga,Tafeenko, Viktor
, (2020)
A fast and convenient synthesis and solid-state luminescence properties of new highly-substituted 6-amino-2H-pyran-2-one derivatives is described. These compounds were obtained from inexpensive and available 2-acyl(aroyl)-1,3-dicyano-1,3-bis-methoxycarbonylpropenides via regioselective heterocyclization under the action of sulfuric and hydroiodic acid. Compounds containing 6-amino-2H-pyran-2-one moiety are nearly unstudied, but are of interest for obtaining condensed biologically active compounds based on this scaffold.
A highly efficient protocol for the synthesis of new 3-(α-aroylamido)-4-hydroxycoumarin derivatives using SnCl2-SiO2 nanoparticles under solventfree conditions
Arfavi-Safari, Mona,Anaraki-Ardakani, Hossein,Badri, Rashid,Tahanpesar, Elham
, p. 321 - 324 (2017)
An efficient and simple protocol for the synthesis of the title compounds is described via a one-pot, three-component reaction of 4-hydroxycoumarin, aryl glyoxals and amides, using SnCl2-SiO2 nanoparticles as a heterogeneous catalyst
Iodine-promoted five-component reaction using fragment assembly strategy to construct dihydrooxepines
Zhao, Peng,Wu, Xia,Geng, Xiao,Wang, Can,Wu, Yan-Dong,Wu, An-Xin
, p. 4323 - 4330 (2018)
An iodine-promoted fragment assembly strategy for the synthesis of fused heterocycles has been established. It provides an efficient route to construct pyrazolone-oxepine-pyrazoles from phenylhydrazines, aryl methyl ketones and acetoacetate esters. Notably, acetoacetate esters play two distinct pivotal roles in the five-component reaction by realizing the unique reactivities of methyl, methylene and carbonyl groups to construct 3-methyl-5-pyrazolone skeletons and by the reaction of methyl and carbonyl groups to form a C (sp3)-O bond.
Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones
Amador, Adrian G.,Sherbrook, Evan M.,Yoon, Tehshik P.
, p. 4722 - 4725 (2016)
Control of stereochemistry in photocycloaddition reactions remains a substantial challenge; almost all successful catalytic examples to date have involved [2 + 2] photocycloadditions of enones. We report a method for the asymmetric [3 + 2] photocycloaddition of aryl cyclopropyl ketones that enables the enantiocontrolled construction of densely substituted cyclopentane structures not synthetically accessible using other catalytic methods. These results show that the dual-catalyst strategy developed in our laboratory broadens synthetic chemists' access to classes of photochemical cycloadditions that have not previously been feasible in enantioselective form.
A NEW FACILE SYNTHESIS OF α-DICARBONYL COMPOUNDS BY OXIDATION OF ALKYNES WITH Mo(VI) PEROXOCOMPLEX PROMOTED BY MERCURIC ACETATE
Ballistreri, Francesco P.,Failla, Salvatore,Tomaselli, Gaetano A.,Curci, Ruggero
, p. 5139 - 5142 (1986)
Mercuric acetate promoted oxidation of diaryl-, dialkyl-, and aralkylalkynes with (HMPA)MoO(O2)2 in 1,2-dichloroethane affords the corresponding α-diketones in good yields.Likewise, terminal alkynes can be converted into α-ketoaldehydes in excellent yields by using the same oxidizing system.
