134804-66-3Relevant academic research and scientific papers
Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran
Cao, Tongxiang,Jiang, Huanfeng,Zhang, Ling,Zhu, Shifa
supporting information, p. 4670 - 4677 (2020/02/20)
An unprecedented deconstructive reorganization strategy for the de novo synthesis of hydroxylated benzofurans from kojic acid- or maltol-derived alkynes is reported. In this reaction, both the benzene and furan rings were simultaneously constructed, whereas the pyrone moiety of the kojic acid or maltol was deconstructed and then reorganized into the benzene ring as a six-carbon component. Through this strategy, at least one free hydroxyl group was introduced into the benzene ring in a substitution-pattern tunable fashion without protection–deprotection and redox adjustment. With this method, a large number of hydroxylated benzofuran derivatives with different substitution-patterns have been prepared efficiently. This methodology has also been shown as the key step in a collective total synthesis of hydroxylated benzofuran-containing natural products (11 examples).
Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N′-Acyl Arylhydrazines
Cao, Jun,Chen, Zi-Li,Li, Shu-Min,Zhu, Gao-Feng,Yang, Yuan-Yong,Wang, Cong,Chen, Wen-Zhang,Wang, Jian-Ta,Zhang, Ji-Quan,Tang, Lei
, p. 2774 - 2779 (2018/06/21)
A novel ligand-free palladium-catalyzed C-2 arylation of benzofurans has been developed using N′-acyl arylhydrazines as the coupling partners and TEMPO as an oxidant. This protocol features a wide functional-group tolerance and highly regioselective products with good to excellent yields.
Arylation synthesis method for novel five-membered aromatic heterocycle and aromatic-ring five-membered aromatic heterocycle
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Paragraph 0112-0115; 0240-0243, (2018/07/07)
The invention belongs to the technical field of organic synthesis and in particular relates to an arylation synthesis method for a five-membered aromatic heterocycle or an aromatic-ring five-memberedaromatic heterocycle under the participation of an arylhydrazine derivative serving as a novel arylation reagent. The method comprises the steps: adding a raw material and aroyl hydrazine into a reactor, and carrying out a reaction at 60-100 DEG C for 8-24h under the condition that an oxidant and a transition metal catalyst are added; after the reaction is ended, carrying out suction filtration, extracting a filtrate by using ethyl acetate, carrying out drying to obtain a crude product of a target compound, and carrying out column chromatography on silica gel to obtain a pure product of the target compound. The arylation synthesis method for the five-membered aromatic heterocycle or the aromatic-ring five-membered aromatic heterocycle is scientific and reasonable and has the advantages such as simplicity and convenience in operation, relatively high yield and simplicity in amplification and purification.
Regioselective preparation of benzo[b]furans from Phenols and α-Bromoketones
Arias, Leire,Vara, Yosu,Cossio, Fernando P.
experimental part, p. 266 - 275 (2012/02/05)
In this paper, a fully regiocontrolled synthesis of either 2- and 3-substituted benzo[b]furans is described. Direct reaction between phenols and α-bromoacetophenones in the presence of neutral alumina yields 2-substituted benzo[b]furans with complete regiocontrol. When a basic salt such as potassium carbonate is used, the corresponding 2-oxoether is obtained. Cyclization of these latter compounds promoted by neutral alumina yields the corresponding 3-substituted benzo[b]furans. Using the former method, Moracin M and other analogues can be obtained from commercial sources in two preparative steps. DFT calculations provide reasonable reaction paths to understand the formation of 2-substituted benzo[b]furans.
Synthesis and antimicrobial evaluation of 3-methanone-6-substituted- benzofuran derivatives
Liu, Jingbao,Jiang, Faqin,Jiang, Xizhen,Zhang, Wei,Liu, Jingjing,Liu, Wenlu,Fu, Lei
, p. 879 - 886 (2012/09/10)
Seventeen benzofuran derivatives were synthesized and screened for their antibacterial activities against Escherichia coli, Staphylococcus aureus, Methicillin-resistant S. aureus, Bacillus subtilis, and Pseudomonas aeruginosa. Seven of them have showed excellent antibacterial activities compared to the positive controls (Cefotaxime and Sodium Penicillin). The substitutions at C-6 and C-3 positions of these derivatives were found to greatly impact on the antibacterial activity and strains specificity, respectively. Specifically, compounds bearing a hydroxyl group at C-6 (5a, 5b, 5c and 12) offered excellent antibacterial activities against all five above-mentioned strains (MIC 80 = 0.78-12.5 ug/mL), and those with imine (15) and (3, 4, 5-trimethoxyphenyl) methanone (7e), respectively, at C-3 position showed selective activity against S. aureus among five tested strains with great MIC80 values (3.12-12.5 ug/mL).
Synthesis of 2-arylbenzofuran phytoalexins
Meyer, M.,Deschamps, C.,Molho, D.
, p. 91 - 99 (2007/10/02)
A new synthesis of 2-arylbenzofuran using direct oxidative rearrangement of 2-benzyloxychalcones by Tl(ONO2)3 followed by cyclization of the key intermediates: 2-benzyloxypropan-1-ones is described.The method has been applied to the synthesis of six 2-ary
Transition Metal Directed Synthesis of Moracin M, a Phytoalexin of Morus alba Linn.
Mann, Inderjit S.,Widdowson, David A.,Clough, John M.
, p. 7981 - 7990 (2007/10/02)
2-(5-Resorcinyl)benzofurans have been synthesised by the palladium catalysed cross coupling of 2-trimethylstannyl- or 2-bromozinc benzofurans with the appropriately functionalised 5-iodoresorcinols.These were synthesised by the tri-isopropylsilyloxy direc
