40484-98-8Relevant articles and documents
De novo synthesis of benzofurans via trifluoroacetic acid catalyzed cyclization/oxidative aromatization cascade reaction of 2-hydroxy-1,4-diones
Sha, Qiang,Liu, Haixuan
, p. 7547 - 7551 (2019/08/20)
A facile, one-pot method for the de novo synthesis of benzofurans from 2-hydroxy-1,4-diones is described. Using trifluoroacetic acid (TFA) as the catalyst and N-bromobutanimide (NBS) as the oxidant, 2-hydroxy-1,4-diones underwent a cyclization/oxidative a
Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds
Huang, Wenbo,Xu, Jing,Liu, Changhui,Chen, Zhiyan,Gu, Yanlong
, p. 2941 - 2950 (2019/02/26)
2,3-Disubstituted benzofurans were synthesized from acrolein dimer and 1,3-dicarbonyl compounds by using N-bromosuccinimide as an oxidizing agent. The method was used to synthesize two commercial drug molecules, benzbromarone and amiodarone. The proposed mechanism of the reaction involves a N-bromosuccinimide (NBS)-assisted autotandem catalysis with Lewis acid catalyst. To proof the proposed mechanism, an intermediate was isolated successfully, which can be converted to 4,5,6,7-tetrahydrobenzofurans.
Synthesis of oxacalothrixin B and its analogues involving iodine/TBHP-mediated electrocyclization
Ramalingam, Bose Muthu,Mohanakrishnan, Arasambattu K.
, p. 2919 - 2922 (2017/07/11)
The total synthesis of oxacalothrixins, an isostere of biologically important carbazoloquinone alkaloid, calothrixin B was achieved from 2-acetyl-3-methylbenzofuran. An iodine/TBHP-mediated oxidative cyclization of benzofuranyl-enamine has been employed as a key step to synthesize, the crucial intermediate 1-hydroxy dibenzofurancarbaldehyde. The latter upon reductive cyclization followed by PIDA-mediated oxidation furnished oxacalothrixin B and its analogues.
Palladium-Catalyzed Oxidative Cycloisomerization of 2-Cinnamyl-1,3-Dicarbonyls: Synthesis of Functionalized 2-Benzyl Furans
Nallagonda, Rajender,Reddy, Reddy Rajasekhar,Ghorai, Prasanta
supporting information, p. 14732 - 14736 (2015/10/19)
A new palladium-catalyzed intramolecular oxidative cycloisomerization of readily available starting materials, 2-cinnamyl-1,3-dicarbonyls, has been demonstrated for the creation of structurally diverse 2-benzyl furans. The cycloisomerization occurs by a regioselective 5-exo-trig pathway. The reaction shows a broad substrate scope with good to excellent yields. Furthermore, a one-pot procedure has been executed by using readily available cinnamyl alcohols and 1,3-diketones. Cinnamyl verit: Palladium-catalyzed intramolecular oxidative cycloisomerization of readily available 2-cinnamyl-1,3-dicarbonyls affords structurally diverse 2-benzyl furans. The cycloisomerization occurs by a regioselective 5-exo-trig pathway, with a broad substrate scope in good to excellent yields. Furthermore, a one-pot procedure is executed by using readily available cinnamyl alcohols and 1,3-diketones
Reporting the release of caged species by a combination of two sequential photoreactions, a molecular switch, and one color of light
Wu, Tuoqi,Tang, Hao,Bohne, Cornelia,Branda, Neil R.
supporting information; experimental part, p. 2741 - 2744 (2012/05/04)
In the right light: UV light triggers bond breaking, liberates a caged carboxylic acid, and generates the central C=C double bond in the photoresponsive hexatriene molecule of a dithienylethene molecular switch. Light of the same wavelength converts the colorless isomer into its colored counterpart (see picture) in a visually convenient method to report on the success of the release event. Copyright
Cu-catalyzed reaction of 1,2-dihalobenzenes with 1,3-cyclohexanediones for the synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones
Aljaar, Nayyef,Malakar, Chandi C.,Conrad, Juergen,Strobel, Sabine,Schleid, Thomas,Beifuss, Uwe
, p. 7793 - 7803 (2013/01/15)
The Cu(I)-catalyzed reaction of 1-bromo-2- iodobenzenes and other 1,2-dihalobenzenes with 1,3-cyclohexanediones in DMF at 130 °C using Cs 2CO3 as a base and pivalic acid as an additive selectively delivers 3,4- dihydrodibenzo[b,d]fur
Gold(III)-catalyzed tandem reaction of O-arylhydroxylamines with 1,3-dicarbonyl compounds: Highly selective synthesis of 3-carbonylated benzofuran derivatives
Liu, Yunkui,Qian, Jianqiang,Lou, Shaojie,Xu, Zhenyuan
supporting information; experimental part, p. 6300 - 6303 (2010/11/18)
Figure presented. A highly regioselective protocol for the synthesis of 3-carbonylated benzofuran derivatives has been developed involving the gold(III)-catalyzed tandem condensation/rearrangement/cyclization reaction of O-arylhydroxylamines with 1,3-dicarbonyl compounds.
Cycloaddition of arynes with lodonium ylides: A mild and general route for the synthesis of benzofuran derivatives
Huang, Xiao-Cheng,Liu, Yi-Lin,Liang, Yun,Pi, Shao-Feng,Wang, Feng,Li, Jin-Heng
supporting information; experimental part, p. 1525 - 1528 (2009/04/07)
A mild and general cycloaddition of arynes with iodonium ylides protocol has been developed for the synthesis of benzofurans. In the presence of CsF, ortho-silyl aryltriflates were reacted with iodonium ylides smoothly at room temperature in moderate to good yields.
Naturally Occurring Dibenzofurans. Part 4. Synthesis of Dibenzofurandiols by Annelation of Benzofurans
Carvalho, Christopher F.,Sargent, Melvyn V.
, p. 1605 - 1612 (2007/10/02)
Methyl 3-acetylbenzofuran-2-ylacetate (8) undergoes C-methylation affording methyl 2-(3-acetylbenzofuran-2-yl)propionate (13).These compounds and similar oxo esters undergo ready cyclization to dibenzofurandiols on treatment with sodium methoxide in boiling methanol.A convenient synthesis of dimethyl furan-2,5-diylacetate (30) is described, as are attempts to synthesize 1,3,7,9-tetramethoxy-2,8-dimethyldibenzofuran (3).
