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Upstream product

• 100-42-5 styrene 
• 504-02-9 1,3-cylohexanedione 
• 66981-69-9 2-(Dimethyl-λ⁴-sulfanylidene)-1-phenyl-propan-1-one 
• 1620143-03-4 1-phenylspiro-[2.5]octane-4,8-dione 
• 75326-15-7 (2-bromo-1-phenylethyl)dimethylsulphonium bromide 
• 86396-02-3 2-(phenyl-λ³-iodaneylidene)cyclohexane-1,3-dione 
• 96-09-3 styrene oxide 
• 1460-08-8 2-diazocyclohexane-1,3-dione 
• 6648-30-2 2,2-dibromo-1,3-cyclohexanedione 

Relevant academic research and scientific papers

Iodide-Catalyzed Ring-Opening Cyclization of Cyclohexane-1,3-dione-2-spirocyclopropanes

The ring-opening cyclization of 2′,3′-nonsubstituted and 2′-electron-withdrawing group (EWG)-substituted cyclohexane-1,3-dione-2-spirocyclopropanes was accomplished using iodide as a catalyst. The nonsubstituted derivatives afforded 3,5,6,7-tetrahydro-1-benzofuran-4(2H)-ones in high yields in the presence of trimethylsilyl iodide at room temperature. The EWG-substituted spirocyclopropanes, in turn, underwent regioselective ring opening followed by cyclization, which gave rise to 2-substituted tetrahydrobenzofuran-4-ones when a combination of tetrabutylammonium iodide catalyst and trifluoromethanesulfonic acid was used, whereas calcium iodide afforded the 3-substituted derivatives. (Figure presented.).

Ring-opening cyclization of spirocyclopropanes with stabilized sulfonium ylides for the construction of a chromane skeleton

Regioselective ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes with stabilized sulfonium ylides provided 2,3-trans-disubstituted 2,3,4,6,7,8-hexahydro-5H-1-benzopyran-5-ones in high yields without the formation of any isomers. The o

Acid-Catalyzed Ring-Opening Cyclization of Spirocyclopropanes for the Construction of a 2-Arylbenzofuran Skeleton: Total Synthesis of Cuspidan B

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

Cooperative Indium(III)/Silver(I) System for Oxidative Coupling/Annulation of 1,3-Dicarbonyls and Styrenes: Construction of Five-Membered Heterocycles

A cooperative indium(III)/silver(I) system for the synthesis of various five-membered heterocycles, including dihydrofurans, pyrroles, spirolactones, and spiroiminolactones, through the sequential oxidative coupling/annulation reaction of 1,3-dicarbonyl compounds with styrenes has been developed. Four different heterocyclic systems were successfully synthesized depending on the substitution pattern of the substrates using readily available starting materials. This system has the advantages of a broad substrate scope, moderate to good chemical yields, an operationally easy and simple procedure, and short reaction times. (Figure presented.) .

One-pot Synthesis of Dihydrofuran Derivatives by Ru Catalyzed Reaction

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

Metal-catalyzed thermal reactions of cyclic β-Dicarbonyl Phenyliodonium Ylide with Styrenes

A cyclic β-dicarbonyl phenyliodonium ylide reacted with various substituted styrenes under Rh2(OAc)4 catalysis to give cyclopropanes and dihydrofurans in a highly regioselective fashion. When styrenes with electron-donating substituents or disubstituted were employed, only dihydrofurans were isolated instead. A mechanism involving two competing pathways rationalizes the results.

Potassium Persulfate Mediated Oxidative Radical Cyclization of 1,3-Dicarbonyl Compounds with Styrenes for the Synthesis of Dihydrofurans

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.

An efficient synthesis of cycloalkane-1,3-dione-2-spirocyclopropanes from 1,3-cycloalkanediones using (1-aryl-2-bromoethyl)-dimethylsulfonium bromides: Application to a one-pot synthesis of tetrahydroindol-4(5H)-one

An efficient synthesis of cyclohexane- and cyclopentane-1,3-dione-2-spirocyclopropanes from 1,3-cycloalkanediones using sulfonium salts was achieved. The reaction of 1,3-cycloalkanediones with (1-aryl-2-bromoethyl)-dimethylsulfonium bromides and powdered K2CO3 in EtOAc provided the corresponding spirocyclopropanes in high yields. Furthermore, a one-pot synthesis of tetrahydroindol-4(5H)-one from 1,3-cyclohexanedione was achieved using the present protocol and a sequential ring-opening cyclization of spirocyclopropane with a primary amine.

Fused dihydrofurans from the one-pot, three-component reaction of 1,3-cyclohexanedione, iodobenzene diacetate and alkenes

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

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.