- Rapid and Multigram Synthesis of Vinylogous Esters under Continuous Flow: An Access to Transetherification and Reverse Reaction of Vinylogous Esters
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An environmentally benign approach for the synthesis of vinylogous esters from 1,3-diketone and its reverse reaction under continuous-flow has been developed with alcohols in the presence of inexpensive Amberlyst-15 as a catalyst. This methodology is highly selective and general for a range of cyclic 1,3-dicarbonyl compounds which gives a library of linear alkylated and arylated vinylogous esters in good to excellent yield under solvent and metal free condition. Furthermore, the long-time experiment in a continuous-flow up to 40 h afforded 8.0 g of the vinylogous ester with turnover number (TON) = 28.6 and turnover frequency (TOF) = 0.715 h-1 using Amberlyst-15 as a catalyst. Furthermore, a continuous-flow sequential transetherification of vinylogous esters with various alcohols has been achieved in high yield. Reversibly, this vinylogous ester was deprotected or hydrolyzed into ketone using environmentally benign water as a solvent and Amberlyst-15 as a catalyst under continuous-flow process.
- Mohanta, Nirmala,Chaudhari, Moreshwar B.,Digrawal, Naveen Kumar,Gnanaprakasam, Boopathy
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p. 1034 - 1045
(2019/05/24)
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- Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones
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The one-pot cyclization of 5-hexynoic acid to produce 3-alkoxy-2- cyclohexenones proceeds in good yields (58-90%). 3-Hexynoic acid was converted to its acyl chloride with the aid of oxalyl chloride and was cyclized to 3-chloro-2-cyclohexenone upon addition of indium(III) chloride. Subsequent addition of alcohol nucleophiles led to the desired 3-alkoxy-2-cyclohexenones.
- Hylden, Anne T.,Uzelac, Eric J.,Ostojic, Zeljko,Wu, Ting-Ting,Sacry, Keely L.,Sacry, Krista L.,Xi, Lin,Jones, T. Nicholas
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experimental part
p. 1323 - 1326
(2011/11/06)
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- Iron(III) tosylate in the preparation of dimethyl and diethyl acetals from ketones and β-keto enol ethers from cyclic β-diketones
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An efficient method for conversion of ketones to their corresponding dimethyl and diethyl acetals and of cyclic β-diketones into β-keto enol ethers using Fe(OTs)3 as a catalyst is described. Copyright Taylor & Francis Group, LLC.
- Mansilla, Horacio,Afonso, Maria M.
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p. 2607 - 2618
(2008/12/22)
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- An efficient conversion of β-diketones into β-keto enol ethers with P2O5/SiO2 under solvent-free conditions
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P2O5/SiO2 was found to be an efficient reagent for converting cyclic-β-diketones into their corresponding β-keto enol ethers at room temperature under solvent-free conditions.
- Cui, Zhen-Shui,Zhang, Zhan-Hui,Liu, Shu-Fen
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p. 390 - 392
(2007/10/03)
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- Cerium(IV) ammonium nitrate-catalyzed synthesis of β-keto enol ethers from cyclic β-diketones and their deprotection
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A mild and efficient method for etherification of cyclic β-diketones with alcohols has been developed using a catalytic amount of cerium(IV) ammonium nitrate at room temperature to afford the corresponding β-keto enol ethers in good to excellent yields. The deprotections of enol ethers in water-acetonitrile (1:1) using a catalytic amount (10 mol %) of cerium(IV) ammonium nitrate have also been achieved. Copyright
- Banerjee, Biplab,Mandal, Samir Kumar,Roy, Subhas Chandra
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- METHOD FOR PRODUCING SUBSTITUTED VINYL ETHER DERIVATIVE
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PROBLEM TO BE SOLVED: To provide a method for producing a substituted vinyl ether derivative by ether exchange from a substituted vinyl ether which has an electron-attracting group as a substituent on a double bond carbon atom to cause the binding site to be electron-deficient. SOLUTION: The method for producing a substituted vinyl ether derivative comprises subjecting a substituted vinyl ether, which has at least one electron-attracting group as a substituent on a carbon atom which forms carbon-carbon double bond, to ether exchange reaction with an alcohol or a phenol in the presence of a catalyst containing a compound of the group 9 and/or 10 metal in the periodic table, wherein the compound has a counter anion, and when the anion is protonated, the proton has an ionization constant (pKa) of 0 or less.
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Page/Page column 9
(2008/06/13)
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- Solvent free rapid synthesis of 3-alkoxycyclohex-2-en-1-one from 1,3-cyclohexanedione promoted by indium(in) chloride/silica gel
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A convenient and environmentally friendly method for the synthesis of 3-alkoxycyclohex-2-en-1-one 1 from cyclohexane-1,3-dioneonthe surface of silica gel impregnated with indium(III) chloride under microwave irradiation without any solvent has been reported CSIRO 2005.
- Murugan,Kamakshi,Reddy, Boreddy S. R.
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p. 228 - 230
(2008/02/04)
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- Microwave assisted rapid synthesis of 3-alkoxy-2-cyclohexen-1-ones from 1,3-cyclohexanedione
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Synthesis of 3-alkoxy-2-cyclohexen-1-ones from 1,3-cyclohexanedione with various alcohols has been achieved under microwave irradiation conditions within 7 min.
- Murugan,Reddy
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p. 1512 - 1514
(2007/10/03)
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- Iodine-catalyzed synthesis of β-keto enol ethers
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The use of iodine, as a catalyst for the synthesis of β-keto enol ethers at room temperature is reported. The use of iodine, as a catalyst for the synthesis of β-keto enol ethers at room temperature is reported.
- Bhosale, Rajesh S.,Bhosale, Sidhanath V.,Bhosale, Sheshanath V.,Wang, Tianyu,Zubaidha
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p. 7187 - 7188
(2007/10/03)
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- SYNTHESIS OF SPIROETHERS USING RADICAL CYCLISATIONS
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A variety of spiroether products, including one bis-spiro compound, are avaible via a simple radical cyclisation route.
- Middleton, Donald S.,Simpkins, Nigel S.,Begley, Michael J.,Terrett, Nicholas K.
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p. 545 - 564
(2007/10/02)
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