92912-81-7Relevant articles and documents
Diacetoxyiodobenzene-mediated oxidative addition of 1,3-dicarbonyl compounds to olefins: An efficient one-pot synthesis of 2,3-dihydrofuran derivatives
Karade,Shirodkar,Patil,Potrekar,Karade
, p. 6729 - 6731 (2003)
A variety of olefins react with -dicarbonyl compounds at 0°C in the presence of diacetoxyiodobenzene to afford highly substituted 2,3-dihydrofuran derivatives in good to excellent yields.
Mono- and binuclear copper(I) complexes of thionucleotide analogues and their catalytic activity on the synthesis of dihydrofurans
Charalampou,Kourkoumelis,Karanestora,Hadjiarapoglou,Dokorou,Skoulika,Owczarzak,Kubicki,Hadjikakou
, p. 8322 - 8333 (2014)
The reaction of copper(I) halides with 2-thiouracil (TUC), 6-methyl-2-thiouacil (MTUC), and 4-methyl-2-mercaptopyrimidine (MPMTH) in the presence of triphenylphosphine (tpp) in a 1:1:2 molar ratio results in a mixed-ligand copper(I) complex with the formulas [Cu2(tpp) 4(TUC)Cl] (1), [Cu2(tpp)4(MTUC)Cl] (2), [Cu(tpp)2(MPMTH)Cl]·1/2CH3OH (3), [Cu(tpp)2(MTUC)Br] (4), and [Cu(tpp)2(MTUC)I] ·1/2CH3CN (5). The complexes have been characterized by FT-IR, 1H NMR, and UV-vis spectroscopic techniques and single-crystal X-ray crystallography. Complexes 1 and 2 are binuclear copper(I) complexes. Two phosphorus atoms from tpp ligands are coordinated to the copper(I) ions, forming two units that are linked to each other by a deprotonated TUC or MTUC chelating ligand through a sulfur bridge. A linear Cu-S-Cu moiety is formed. The tetrahedral geometry around the metal centers is completed by the nitrogen-donor atom from the TUC or MTUC ligand for the one unit, while for the other one, it is completed by the chloride anion. Two phosphorus atoms from two tpp ligands, one sulfur atom from MPMTH or MTUC ligand, and one halide anion (Cl, Br, and I) form a tetrahedron around the copper ion in 3-5 and two polymorphic forms of 4 (4a and 4b). In all of the complexes, either mono- or binuclear intramolecular O-H...X hydrogen bonds enhance the stability of the structures. On the other hand, in almost all cases of mononuclear complexes (with the exception of a symmetry-independent molecule in 4a), intermolecular NH...O hydrogen-bonding interactions lead to dimerization. Complexes 1-5 were studied for their catalytic activity for the intermolecular cycloaddition of iodonium ylides toward dihydrofuran formation by HPLC, 1H NMR, and LC-HRMS spectroscopic techniques. The results show that the geometry and halogen and ligand types have a strong effect on the catalytic properties of the complexes. The highest yield of dihydrofurans was obtained when linear complexes 1 and 2 were used as the catalysts. The activity of the metal complexes on the copper(I)-catalyzed and uncatalyzed intramolecular cycloaddition of iodonium ylide is rationalized through electronic structure calculation methods, and the results are compared with the experimental ones.
Acid-Catalyzed Ring-Opening Cyclization of Spirocyclopropanes for the Construction of a 2-Arylbenzofuran Skeleton: Total Synthesis of Cuspidan B
Nambu, Hisanori,Ono, Naoki,Yakura, Takayuki
, p. 1892 - 1901 (2016/06/15)
Acid-catalyzed ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes under metal-free conditions proceeded smoothly at room temperature to provide 2-aryl-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-ones in excellent yields without the formation
One-pot Synthesis of Dihydrofuran Derivatives by Ru Catalyzed Reaction
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Paragraph 0071-0075, (2016/10/10)
The present invention relates to a one-pot synthesis method of dihydrofuran derivatives using a ruthenium catalyst and, more particularly, to a one-pot synthesis method of dihydrofuran derivatives, which makes a reaction between cyclic/non-cyclic diazo dicarbonyl compound and olefin in the presence of ruthenium (II) phosphine complex as a reaction catalyst. The one-pot synthesis method of the present invention shortens time required for the reaction and improves synthesis yield. The diazo carbonyl compound represented by chemical formula 1, 2, or 3 reacts with olefin to form dihydrofuran derivatives through a [3+2] cyclization addition reaction.COPYRIGHT KIPO 2016
Potassium Persulfate Mediated Oxidative Radical Cyclization of 1,3-Dicarbonyl Compounds with Styrenes for the Synthesis of Dihydrofurans
Wang, Shun,He, Lin-Ye,Guo, Li-Na
, p. 3191 - 3197 (2015/10/19)
A potassium persulfate promoted tandem radical addition/cyclization of 1,3-dicarbonyl compounds with styrenes has been developed. This transition-metal-free procedure provides an efficient approach to a diverse set of substituted dihydrofurans in moderate to good yields.
Fused dihydrofurans from the one-pot, three-component reaction of 1,3-cyclohexanedione, iodobenzene diacetate and alkenes
Kalpogiannaki, Dimitra,Martini, Catherine-Irene,Nikopoulou, Aggeliki,Nyxas, John A.,Pantazi, Vassiliki,Hadjiarapoglou, Lazaros P.
, p. 1566 - 1575 (2013/02/25)
The one-pot, three-component reactions of substituted 1,3- cyclohexanediones, iodobenzene diacetate and alkenes, under photochemical activation, yields fused dihydrofuran derivatives in good yield via the in situ formation of iodonium ylides.
Efficient one-pot synthesis of multi-substituted dihydrofurans by ruthenium(II)-catalyzed [3+2] cycloaddition of cyclic or acyclic diazodicarbonyl compounds with olefins
Xia, Likai,Lee, Yong Rok
, p. 2361 - 2374 (2013/10/01)
Ruthenium(II)-phosphine complexes-catalyzed [3+2] cycloadditions were conducted to synthesize a variety of dihydrofurans by reactions of cyclic or acyclic diazodicarbonyl compounds with olefins. This method represents a direct and efficient one-pot synthesis for multi-substituted dihydrofurans under mild reaction conditions with an excellent regioselectivity. Furthermore, to reduce reaction times and increase yields of dihydrofurans, microwave-as sisted tris(triphenylphosphine)ruthenium(II) chloride/ 1-butyl-3-methylimidazolium tetrafluoroborate {Ru (PPh3)3Cl2/ [Bmim]BF4}-catalyzed reactions were also developed. The synthesized dihydrofurans can be readily converted into biologically interesting tetrahydroindoles.
Synthesis and structural characterization of new cu(I) complexes with the antithyroid drug 6-n-propyl-thiouracil. Study of the cu(I)-catalyzed intermolecular cycloaddition of iodonium ylides toward benzo[b]furans with pharmaceutical implementations
Paizanos,Charalampou,Kourkoumelis,Kalpogiannaki,Hadjiarapoglou,Spanopoulou,Lazarou,Manos,Tasiopoulos,Kubicki,Hadjikakou
, p. 12248 - 12259 (2013/01/15)
The reaction of copper(I) iodide with 6-n-propylthiouracil (ptu) in the presence or absence of the triphenylphosphine (tpp) or tri(p-tolyl)phosphine (tptp) in a 1:1:2 molar ratio forms the mixed ligand Cu(I) complex with formula [CuI(ptu)2](tol
An organocatalyzed highly regioselective one-pot approach to the synthesis of tetrahydrobenzofuranones
Chawla, Ruchi,Singh, Atul K.,Yadav, Lal Dhar S.
experimental part, p. 3382 - 3384 (2012/07/28)
An organocatalyzed highly regioselective synthesis of substituted tetrahydrobenzofuran-4-ones based on the ring opening followed by cyclization of epoxides with enamines of 1,3-cyclohexanediones in a domino fashion is described. It is a high yielding (74-93%) synthetic protocol tolerant to a wide range of substrates. Ambient temperature, organocatalytic approach, atom-economy, and formation of water as the only by-product are some of the attractive features of the present methodology.
AgBF4/[Bmim]BF4-Catalyzed [3+2] cycloaddition of cyclic diazodicarbonyl compounds: Efficient synthesis of 2,3-dihydrofurans and conversion to 3-acylfurans
Xia, Likai,Lee, Yong Rok,Kim, Sung Hong,Lyoo, Won Seok
experimental part, p. 1554 - 1558 (2011/12/14)
A novel and efficient method for the synthesis of 2,3-dihydrofurans bearing a variety of substituents on the dihydrofuran ring was achieved by the reaction of cyclic diazodicarbonyl compounds with styrene and vinyl acetate. The key strategy was AgBF4
