Ring-Closing Metathesis as Methodology for the Synthesis of 2-and 3-Arylbenzo[b]furans

被引:0
作者
Visser, Melanie [1 ]
Twigge, Linette [1 ]
Marais, Charlene [1 ]
Bezuidenhoudt, Barend C. B. [1 ]
机构
[1] Univ Free State, Dept Chem, POB 339, ZA-9300 Bloemfontein, South Africa
来源
SYNTHESIS-STUTTGART | 2024年 / 56卷 / 22期
基金
新加坡国家研究基金会;
关键词
arylbenzofurans; metathesis; Grubbs catalyst; allylation; Tebbe methylenation; Grignard reagent; Al(OTf)(3); BIOACTIVE BENZOFURAN DERIVATIVES; CYCLIC ENOL ETHERS; CLAISEN REARRANGEMENT; CONVENIENT SYNTHESIS; EFFICIENT SYNTHESIS; CARBONYL-COMPOUNDS; PHENOLS; LITHIATION; REAGENT; ACID;
D O I
10.1055/a-2367-2151
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Olefin metathesis, which is well established in the petrochemical industry, is also emerging as a green technology in the manufacture of pharmaceutical and specialty chemicals. Arylbenzofurans are of interest for potential medicinal applications. In this paper we report on the synthesis of various 2-aryl- and 3-arylbenzo[ b ]furans with natural substitution patterns from readily available starting materials in a strategy that applies ring-closing metathesis with the Grubbs second generation catalyst as key step.
引用
收藏
页码:3488 / 3502
页数:15
相关论文
共 70 条
[1]   Anticancer therapeutic potential of benzofuran scaffolds [J].
Abbas, Ashraf A. ;
Dawood, Kamal M. .
RSC ADVANCES, 2023, 13 (16) :11096-11120
[2]   Convenient Synthesis and Antimicrobial Activity of New 3-Substituted 5-(Benzofuran-2-yl)-pyrazole Derivatives [J].
Abdel-Wahab, Bakr F. ;
Abdel-Aziz, Hatem A. ;
Ahmed, Essam M. .
ARCHIV DER PHARMAZIE, 2008, 341 (11) :734-739
[3]   SYNTHESIS OF BENZOFURAN DERIVATIVES VIA DIFFERENT METHODS [J].
Abu-Hashem, Ameen A. ;
Hussein, Hoda A. R. ;
Aly, Ahmed S. ;
Gouda, Moustafa A. .
SYNTHETIC COMMUNICATIONS, 2014, 44 (16) :2285-2312
[4]   Regioselective Preparation of Benzo[b]furans from Phenols and α-Bromoketones [J].
Arias, Leire ;
Vara, Yosu ;
Cossio, Fernando P. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01) :266-275
[5]   3,3′-Bis(arylbenzofurans) via a Gold-Catalyzed Domino Process [J].
Auzias, Mathieu G. ;
Neuburger, Markus ;
Wegner, Hermann A. .
SYNLETT, 2010, (16) :2443-2448
[6]   Domino rhodium(I)-catalysed reactions for the efficient synthesis of substituted benzofurans and indoles [J].
Boyer, Alistair ;
Isono, Naohiro ;
Lackner, Sebastian ;
Lautens, Mark .
TETRAHEDRON, 2010, 66 (33) :6468-6482
[7]   INTRAMOLECULAR [2 + 2] CYCLOADDITION REACTIONS OF KETENE AND CARBONYL GROUPS - A NEW SYNTHESIS OF BENZOFURANS [J].
BRADY, WT ;
GIANG, YF .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (11) :2145-2147
[8]   INTRAMOLECULAR [2+2] CYCLOADDITIONS OF KETENES TO CARBONYL GROUPS - A NOVEL SYNTHESIS OF SUBSTITUTED BENZOFURANS [J].
BRADY, WT ;
GIANG, YSF ;
MARCHAND, AP ;
WU, AH .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3457-3461
[9]   Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N-Acyl Arylhydrazines [J].
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 .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (22) :2774-2779
[10]   Claisen rearrangement over the past nine decades [J].
Castro, AMM .
CHEMICAL REVIEWS, 2004, 104 (06) :2939-3002