19803-11-3Relevant articles and documents
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.
Benzofuran liquid crystal compound and composition thereof
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Paragraph 0050; 0051; 0052, (2018/04/01)
The invention discloses a benzofuran liquid crystal compound containing a benzofuran ring. The structural general formula of the liquid crystal compound is (shown in the description), wherein R represents either one of the straight-chain paraffin with the
One-pot synthesis of 2,3-disubstituted benzofurans from 2-chlorophenols using palladium–dihydroxyterphenylphosphine catalyst
Yamaguchi, Miyuki,Ozawa, Hayato,Katsumata, Haruka,Akiyama, Tomoyo,Manabe, Kei
supporting information, p. 3175 - 3178 (2018/07/15)
2,3-Disubstituted benzofurans possessing 2-hydroxyphenyl moiety at the C-3 position were synthesized from readily available 2-chlorophenols and terminal alkynes by hydroxy-directed ortho-Sonogashira coupling and subsequent oxypalladation/reductive elimina
Synthesis of Benzofurans from Ketones and 1,4-Benzoquinones
Wu, Fengtian,Bai, Rongxian,Gu, Yanlong
, p. 2307 - 2316 (2016/07/29)
Benzofuran derivatives can be synthesized through the sequential Michael addition and cyclization of 1,3-dicarbonyl compounds with 1,4-benzoquinones. However, ketones are rarely used in this reaction because of their low nucleophilicities. In this study, this problem was solved by utilizing triethyl orthoformate, which enabled the formation of a vinyl ethyl ether as an additive. As a result, the nucleophilicity of ketones increased. Many important 5-hydroxybenzofuran derivatives, which were not readily available by synthesis in the past, were also prepared via these newly established reactions. (Figure presented.) .
Design and synthesis of 2-phenylnaphthalenoids and 2-phenylbenzofuranoids as DNA topoisomerase inhibitors and antitumor agents
Hao, Huilin,Chen, Wang,Zhu, Jing,Lu, Chunhua,Shen, Yuemao
, p. 277 - 287 (2015/09/01)
Abstract Eight 2-phenylnaphthalenoids (2PNs) (3a-h) and twenty four 2-phenylbenzofuranoids (2PBFs) (4a - 4j, 5a-5j, 6a, 6f-6h) were successfully designed, synthesized and their antiproliferative and in vitro DNA topoisomerase inhibitory activities were evaluated. Nine compounds (four 2PNs and five 2PBFs) showed either TopoI or TopoIIα inhibitory activities. Six compounds (four 2PNs and two 2PBFs) exhibited potent cytotoxicity with IC50 values for 72 h exposure ranging from 0.3 to above 20 μM against MDA-MB-231, MDA-MB-435, HepG2 and PC3 cell lines. The two 2PBFs displayed comparable and even better antiproliferative as well as TopoIIα inhibitory activities than 2PNs. Interestingly, the active 2PBFs displayed different mechanisms of TopoIIα inhibition from that of 2PNs, suggesting that the chromophore scaffold replacement may result in a change of the binding site of inhibitors to TopoIIα. Furthermore, the mechanisms of antiproliferation on MDA-MB-231 cells indicate that compounds 5a and 5f are promising for further development of anticancer agents. The results of this study reveal that the evolutionary strategy of medicinal chemistry through scaffold hopping is a promising strategy for structure optimization of TopoIIα inhibitors.
Palladium-catalyzed synthesis of benzofurans and coumarins from phenols and olefins
Sharma, Upendra,Naveen, Togati,Maji, Arun,Manna, Srimanta,Maiti, Debabrata
supporting information, p. 12669 - 12673 (2013/12/04)
Triple C-H functionalization: Palladium-catalyzed synthesis of benzofurans and coumarins by reacting phenols and unactivated olefins is described. The reaction comprises sequential C-H functionalization and shows diverse functional group compatibility. Preliminary mechanistic studies shed light into the possible mechanisms. Copyright
MAO Inhibitory Activity of 2-Arylbenzofurans versus 3-Arylcoumarins: Synthesis, invitro Study, and Docking Calculations
Ferino, Giulio,Cadoni, Enzo,Matos, Maria Joao,Quezada, Elias,Uriarte, Eugenio,Santana, Lourdes,Vilar, Santiago,Tatonetti, Nicholas P.,Yanez, Matilde,Vina, Dolores,Picciau, Carmen,Serra, Silvia,Delogu, Giovanna
, p. 956 - 966 (2013/07/27)
Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. Several 3-arylcoumarin derivatives were previously described as interesting selective MAO-B inhibitors. Preserving the trans-stilbene structure, a series of 2-arylbenzofuran and corresponding 3-arylcoumarin derivatives were synthesized and evaluated as inhibitors of both MAO isoforms, MAO-A and MAO-B. In general, both types of derivatives were found to be selective MAO-B inhibitors, with IC50 values in the nano- to micromolar range. 5-Nitro-2-(4-methoxyphenyl)benzofuran (8) is the most active compound of the benzofuran series, presenting MAO-B selectivity and reversible inhibition (IC50=140nM). 3-(4′-Methoxyphenyl)-6-nitrocoumarin (15), with the same substitution pattern as that of compound 8, was found to be the most active MAO-B inhibitor of the coumarin series (IC50=3nM). However, 3-phenylcoumarin 14 showed activity in the same range (IC50=6nM), is reversible, and also severalfold more selective than compound 15. Docking experiments for the most active compounds into the MAO-B and MAO-A binding pockets highlighted different interactions between the derivative classes (2-arylbenzofurans and 3-arylcoumarins), and provided new information about the enzyme-inhibitor interaction and the potential therapeutic application of these scaffolds.
Highly asymmetric synthesis of (+)-corsifuran A. Elucidation of the electronic requirements in the Ruthenium-NHC catalyzed hydrogenation of benzofurans
Ortega, Nuria,Beiring, Bernhard,Urban, Slawomir,Glorius, Frank
, p. 5185 - 5192 (2012/07/31)
A short and efficient synthesis of ent-corsifuran A by a highly asymmetric hydrogenation of a benzofuran precursor is reported. In addition, the electronic influence of the substituents on the asymmetric hydrogenation of benzofurans is provided. Whereas the hydrogenation of electron-deficient benzofurans was achieved under very mild conditions, the presence of electron-donating groups in the benzofuran required harsher reaction conditions for achieving full conversion to the 2,3-dihydrobenzofuran.
A practicable environmentally benign one-pot synthesis of 2-arylbenzofurans at room temperature
Liao, Lian-Yan,Shen, Gang,Zhang, Xue,Duan, Xin-Fang
experimental part, p. 695 - 701 (2012/04/23)
An environmentallyfriendly one-pot synthesis of 2-arylbenzofurans under ambient temperature has been developed. It features an ortho-hydroxyl group assisted Wittig reaction of substituted salicylaldehyde followed by an in situ oxidative cyclization. Its advantages include readily available and non-hazardous materials, benign reaction conditions (room temperature, green solvent and one-pot manner), easy work-up and high overall yields. Utilizing this methodology, various 2-aryl-benzofurans including four natural products have been synthesized. The Royal Society of Chemistry 2012.
2-substituted benzo[b]furans from (E)-1,2-dichlorovinyl ethers and organoboron reagents: Scope and mechanistic investigations into the one-pot Suzuki coupling/direct arylation
Geary, Laina M.,Hultin, Philip G.
supporting information; experimental part, p. 5563 - 5573 (2010/12/29)
2-Substituted benzo[b]furans can easily be assembled from simple phenols, boronic acids or other organoboron reagents, and trichloroethylene. The overall process requires only two synthetic steps, with the key step being a one-pot sequential Suzuki cross-coupling/direct arylation reaction. The method tolerates many useful functional groups and does not require the installation of any other activating functionality. The modular nature of the process permits the rapid synthesis of many analogues using essentially the same chemistry, of particular value in drug development. Results of kinetic isotope effect studies and investigations into the regioselectivity of the process indicate that the direct arylation step most likely does not involve an electrophilic palladation. The most likely mechanism lies somewhere on the continuum between a C-H bond metathesis and an assisted palladation or concerted metallation-deprotonation pathway. A very efficient modular approach to the construction of benzo[b]furans using trichloroethylene as a scaffold is described. This method gives easy access to highlysubstituted heterocycles in only two synthetic operations, and is especially suitable for rapid construction of compound libraries.
