7182-32-3Relevant academic research and scientific papers
Transition Metal-Free Synthesis of Halobenzo[b]furans from O-Aryl Carbamates via o-Lithiation Reactions
Feberero, Claudia,Renedo, Lorena,Sanz, Roberto,Sedano, Carlos,Suárez-Pantiga, Samuel,Virumbrales, Cintia
, (2022/01/24)
A straightforward and transition metal-free one-pot protocol to synthesize halobenzo[b]furans has been developed employing simple and easily available starting materials such as O-aryl carbamates and alkynylsulfones. The fine-tuning of the different steps involved was key to achieving a successful one-pot procedure. Initially, a directed ortho-lithiation process, which uses the carbamate as the directed metalation group, was crucial in providing access to O-2-alkynylaryl N,N-diethyl carbamates by a direct alkynylation of the o-lithiated carbamate, with arylsulfonylalkynes as electrophilic reagents. Cyclization of the generated o-alkynylaryl carbamates was successfully accomplished through a strategy involving in situ carbamate alkaline hydrolysis under conventional heating or microwave irradiation, coupled with a subsequent heterocyclization step delivering the desired benzo[b]furans. A wide variety of new halobenzo[b]furans has been synthesized and their utility has been demonstrated by their further transformation.
Synthesis and biological evaluation of 2-arylbenzofuran derivatives as potential anti-Alzheimer’s disease agents
Yun, Yinling,Miao, Yuhang,Sun, Xiaoya,Sun, Jie,Wang, Xiaojing
, p. 1346 - 1356 (2021/06/26)
Alzheimer's disease (AD) is a type of progressive dementia caused by degeneration of the nervous system. A single target drug usually does not work well. Therefore, multi-target drugs are designed and developed so that one drug can specifically bind to mu
Room Temperature C-H Arylation of Benzofurans by Aryl Iodides
Mayhugh, Amy L.,Luscombe, Christine K.
supporting information, p. 7079 - 7082 (2021/09/18)
A robust method of room temperature direct arylation for benzofuran is reported. This discovery allows for mild arylation by commercially available aryl iodides with complete C-2 regioselectivity and tolerates a range of functional groups, including heat sensitive groups. Mechanistically, a Heck-type oxyarylation product from a direct arylation process is reported as a key piece of evidence for a carbopalladation intermediate.
Method for synthesizing 2-aryl benzofuran and derivatives thereof
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Paragraph 0017-0020, (2020/05/08)
The invention relates to a method for synthesizing 2-aryl benzofuran and derivatives thereof. According to the method, cheap and easily available 2, 3-dihydrobenzofuran compounds, an organic boron reagent and bromo-aromatic hydrocarbon are taken as raw materials, and a two-step cascade reaction is carried out under mild conditions, so that the 2-aryl benzofuran product can be conveniently prepared. At present, the reported synthesis methods of 2-aryl benzofuran and derivatives thereof mainly have the problems of long synthesis route, expensive raw materials, harsh reaction conditions and the like. Compared with reported methods, the synthesis method has the advantages of specific reaction selectivity, short reaction route and the like, and a convenient and efficient synthesis strategy is provided for laboratory preparation or industrial production of 2-arylbenzofuran products.
Synthesis of Benzo[ b]furans by Intramolecular C-O Bond Formation Using Iron and Copper Catalysis
Henry, Martyn C.,Sutherland, Andrew
, p. 2766 - 2770 (2020/03/30)
One-pot processes for the synthesis of benzo[b]furans from 1-aryl- or 1-alkylketones using nonprecious transition metal catalysts have been developed. Regioselective iron(III)-catalyzed halogenation of the aryl ring, followed by iron- or copper-catalyzed O-arylation allowed the synthesis of various structural analogues, including the benzo[b]furan-derived natural products corsifuran C, moracin F, and caleprunin B.
Arylation synthesis method for novel five-membered aromatic heterocycle and aromatic-ring five-membered aromatic heterocycle
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Paragraph 0112-0115; 0164-0167, (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.
Method for synthesizing benzofuranol derivative by nickel-catalysis of phenethynyl phenol under microwave irradiation
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Paragraph 0025; 0033, (2018/09/11)
The invention discloses a method for synthesizing a benzofuranol derivative by nickel-catalysis of phenethynyl phenol under microwave irradiation; a catalytic amount of catalyst nickel chloride, ligand 1,10-phenanthroline(1,10-Phen), auxiliary catalyst po
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.
Mechanistic Insights on Orthogonal Selectivity in Heterocycle Synthesis
Maji, Arun,Reddi, Yernaidu,Sunoj, Raghavan B.,Maiti, Debabrata
, p. 10111 - 10118 (2018/10/20)
Recently, we have developed a method for catalytic regioselective synthesis of 2-substituted and 3-substituted benzofurans starting from phenols. The choice of reacting partner, olefin versus α,β-unsaturated acid, is critical to dictate the isomeric product formation. Instances are known where these olefinic partners did not complement each other and yield a similar outcome. In the current work, we have addressed this paradox with emphasis on (a) the origin of orthogonal selectivity and (b) the key requirements to expect complementary behavior. Experimental and computational studies provided important mechanistic insights. Electrostatic compatibility during migratory insertion and the positioning of the carboxylic acid moiety in catalytic steps are found to exert a paramount impact in determining the regioselectivity. The study offers a predictable single component tuning tool to control the regioselectivity.
An efficient tandem elimination-cyclization-desulfitative arylation of 2-(gem-dibromovinyl)phenols(thiophenols) with sodium arylsulfinates
Chen, Wei,Li, Pinhua,Miao, Tao,Meng, Ling-Guo,Wang, Lei
supporting information, p. 420 - 424 (2013/02/23)
An efficient tandem elimination-cyclization-desulfitative arylation of 2-(gem-dibromovinyl)phenols(thiophenols) with sodium arylsulfinates has been developed. In the presence of TBAF-PdCl2-Cu(OAc)2-NEt 3, the reactions gen
