- Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights
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Substituted pyrans and furans are core structures found in a wide variety of natural products and biologically active compounds. Herein, we report a practical and mild catalytic method for the synthesis of substituted pyrans and furans using molecular iodine, a simple and inexpensive catalyst. The method described is performed under solvent-free conditions at an ambient temperature and atmosphere, thus offering a facile and practical alternative to currently available reaction protocols. A combination of experimental studies and density functional theory calculations revealed interesting mechanistic insights into this seemingly simple reaction.
- Pace, Domenic P.,Robidas, Rapha?l,Tran, Uyen P. N.,Legault, Claude Y.,Nguyen, Thanh Vinh
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p. 8154 - 8171
(2021/06/28)
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- Preparation of polysubstituted dihydrofurans through a PhI(OAc)2-promoted haloenolcyclization of olefinic dicarbonyl compounds
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A metal-free cyclization of olefinic dicarbonyl compounds for the synthesis of various 5-halomethyl-4,5-dihydrofurans is presented. Using (diacetoxyiodo)benzene as the reaction promoter and halotrimethylsilane as the halogen source, the intramolecular hal
- Liu, Ji,Liu, Qing-Yun,Fang, Xing-Xiao,Liu, Gong-Qing,Ling, Yong
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supporting information
p. 7454 - 7460
(2018/10/24)
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- Method for preparing poly-substituted furan compound by condensing tricarbonyl compound under effect of titanium tetrachloride
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The invention provides a method for preparing a poly-substituted furan compound by condensing a tricarbonyl compound under an effect of titanium tetrachloride. The method comprises the following steps: by taking methylene dichloride or methylbenzene as a solvent, causing the tricarbonyl compound react with titanium tetrachloride while stirring under inert gas shielding, ending the reaction and then separating, thereby acquiring the poly-substituted furan compound. The compounding method provided by the invention has the characteristics of easily acquired raw materials, low cost, mild reaction condition, simple and easily controlled operation, less side reaction, simple post-processing, higher product yield, capability of greatly saving production cost, higher economic benefit and suitability for industrial mass production.
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Paragraph 0064-0066
(2017/11/04)
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- Understanding the Scope of Feist–Bénary Furan Synthesis: Chemoselectivity and Diastereoselectivity of the Reaction Between α-Halo Ketones and β-Dicarbonyl Compounds
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Feist–Bénary furan synthesis, the reaction between α-halocarbonyl and β-dicarbonyl compounds, has been known as an efficient method for generating many different types of furans containing a carbonyl group at C-3. However, it has also been reported that, under similar reaction conditions, intermediate tricarbonyl species could be further converted to alternative furan isomers through the application of a Paal–Knorr synthesis. In this manuscript, we investigate the chemoselectivity and diastereoselectivity of furan synthesis from α-halo ketones and β-dicarbonyl compounds, by carrying out the separation and characterization of the intermediates involved in the reaction. Additionally, a one-pot Feist–Bénary furan synthesis from α-halo ketones and β-dicarbonyl compounds without any base or solvent has also been developed.
- Peng, Yi,Luo, Juan,Feng, Qiang,Tang, Qiang
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p. 5169 - 5179
(2016/10/26)
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- Design, synthesis and antifungal activity of novel furancarboxamide derivatives
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Twenty-seven novel furancarboxamide derivatives with a diphenyl ether moiety were synthesized and evaluated for their antifungal activity against Rhizoctonia solani, Botrytis cirerea, Valsa Mali and Sphaceloma ampelimum. Antifungal bioassay results indicated that most compounds had good or excellent fungicidal activities for R. solani and S. ampelimum at 20 mg L-1. Among synthesized compounds, compound 18e showed a greater inhibitory effect against S. ampelimum, with half maximal effective concentration (EC50) values of 0.020 mg L-1. This strong activity rivals currently used commercial fungicides, such as Boscalid and Carbendazim, and has great potential as a lead compound for future development of novel fungicides.
- Wen, Fang,Jin, Hong,Tao, Ke,Hou, Taiping
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p. 244 - 251
(2016/05/24)
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- Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1)
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All-trans-retinoic acid (ATRA), the biologically active metabolite of vitamin A, is used medicinally for the treatment of hyperproliferative diseases and cancers. However, it is easily metabolized. In this study, the leading compound S8 was found based on virtual screening. To improve the activity of the leading compound S8, a series of novel S8 derivatives were designed, synthesized and evaluated for their in vitro biological activities. All of the prepared compounds showed that substituting the 5-chloro-3-methyl-1-phenyl-1H-pyrazole group for the 2-tertbutyl-5-methylfuran scaffold led to a clear increase in the biological activity. The most promising compound 32, with a CYP26A1 IC50 value of 1.36 μM (compared to liarozole (IC50 = 2.45 μM) and S8 (IC50 = 3.21 μM)) displayed strong inhibitory and differentiation activity against HL60 cells. In addition, the study focused on the effect of β-phenylalanine, which forms the coordination bond with the heme of CYP26A1. These studies suggest that the compound 32 can be used as an appropriate candidate for future development.
- Zhao, Dongmei,Sun, Bin,Ren, Jinhong,Li, Fengrong,Song, Shuai,Lv, Xuejiao,Hao, Chenzhou,Cheng, Maosheng
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p. 1356 - 1365
(2015/03/04)
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- Selective synthesis of 2,5-disubstituted furan-3-carboxylates and the isomeric 2,4-disubstituted furan-3-carboxylates
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An unprecedented Ag2CO3 and DBU mediated cyclization of 3-substituted 2-(2-bromoallyl)-3-oxo-1-carboxylates leading to the formation of 2,5-disubstituted furan-3-carboxylates has been reported. In the absence of a silver salt, the is
- Chen, Panpan,Meng, Yinggao,Yang, Qinghua,Wu, Jie,Xiao, Yuanyuan,Gorja, Dhilli Rao,Song, Chuanjun,Chang, Junbiao
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p. 79906 - 79914
(2015/10/06)
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- Indium-catalyzed synthesis of furans and pyrroles via cyclization of α-propargyl-β-keto esters
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In(OTf)3 or In(NTf2)3 effectively catalyze the cyclo-isomerization reaction of -propargyl - keto esters and their imine analogues to afford trisubstituted furans and pyrroles, respectively. Both terminal and internal alkyn
- Tsuji, Hayato,Yamagata, Ken-Ichi,Ueda, Yasuyuki,Nakamura, Eiichi
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p. 1015 - 1017
(2011/06/17)
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- Ionic liquid as catalyst and reaction medium: A Simple and Efficient Procedure for Paal-Knorr furan synthesis
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The ionic liquid 1-butyl-3-methyl-imidazolium hydrogen sulfate, [bmim]HSO4, efficiently catalyzes Paal-Knorr furan synthesis without any organic solvent. A wide range of aliphatic and aromatic 1,4-diketones easily undergo condensations to form furan derivatives, providing a general and convenient procedure. The Paal-Knorr reaction of ester-substituted 1,4-diketones is first reported. The ionic liquid can be recovered and reused for subsequent runs without any appreciable loss of efficiency.
- Wang, Gangqiang,Guan, Zhi,Tang, Rongchang,He, Yanhong
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experimental part
p. 370 - 377
(2010/04/04)
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- Synthesis of pyrroles by gold(I)-catalyzed amino-claisen rearrangement of N-propargyl enaminone derivatives
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(Figure presented) The cationic N-heterocyclic carbene-gold(I) complex catalyzes the formation of tri- and tetrasubstituted pyrroles via the amino-Claisen rearrangement of N-propargyl β-enaminone derivatives and the cyclization of α-allenyl β-enaminone in
- Saito, Akio,Konishi, Tomoyo,Hanzawa, Yuji
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supporting information; experimental part
p. 372 - 374
(2010/03/25)
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- A simple preparation of ethyl 2,5-dimethylfuran-3-carboxylate and 2,5-dimethylfuran-3,4-dicarboxylic acid from diethyl 2,3-diacetylsuccinate
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(Chemical Equation Presented) A simple preparation of ethyl 2,5-dimethylfuran-3-carboxylate (3), 2,5-dimethylfuran-3,4-dicarboxylic acid (4), and diethyl 2,5-dimethylfuran-3,4-dicarboxylate (5) by treatment of diethyl 2,3-diacetylsuccinate (2) with aqueous HCl is reported. The reaction is performed under organic solvent free conditions from a readily available cheap starting material.
- Wang, Gang-Qiang,Guan, Zhi,Tang, Rong-Chang,Ostojic, Zeljko,Jones, T. Nicholas,Wu, Ting-Ting,He, Yan-Hong
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experimental part
p. 540 - 543
(2009/09/05)
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- Process for the preparation of furan compounds
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A carbonyl compound represented by following Formula (1): wherein R1 represents hydrogen atom or an organic group; and R2 represents hydrogen atom or an organic group having a carbon atom at a bonding site with the carbonyl group in Formula (1), wherein R1 and R2 may be combined to form a ring with adjacent two carbon atoms, or an equivalent thereof is reacted with an unsaturated compound represented by following Formula (2): wherein each of R3, R4, and R5 represents hydrogen atom, a halogen atom, hydroxyl group, or an organic group and wherein R3 and R4 may be combined to form a ring with adjacent two carbon atoms, or a precursor thereof, to yield a furan compound represented by following Formula (3): wherein R3′ represents R3, R5 or hydrogen atom; and R1, R2, R3, R4, are R5 are as defined above.
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Page/Page column 7
(2008/06/13)
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- Gold(I)-catalyzed synthesis of highly substituted furans
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(Chemical Equation Presented) Cationic triphenylphosphinegold(I) complexes are excellent catalysts for a cascade reaction of propargyl-Claisen rearrangement and heterocyclization to synthesize tri- and tetrasubstituted furans. Starting from easily accessed propargyl vinyl ethers, the furans are obtained in 72-99% yield.
- Suhre, Michael H.,Reif, Michael,Kirsch, Stefan F.
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p. 3925 - 3927
(2007/10/03)
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- Polymer-supported selenium-induced electrophilic cyclization: Solid-phase synthesis of poly-substituted dihydrofurans and tetrahydrofurans
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Poly-substituted dihydrofurans and tetrahydrofurans have been synthesized through polymer-supported selenium-induced intramolecular electrophilic cyclization, followed by selenoxide syn-elimination or novel nucleophilic substitution cleavage of selenium resin with good yields and purities. Graphical Abstract
- Tang,Huang, Xian,Xu, Wei-Ming
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p. 9963 - 9969
(2007/10/03)
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- The reactions of diazo compounds with lactones. Part 2. The reaction of cyclic 2-diazo-1,3-dicarbonyl compounds with diketene: Benzofuran formation
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Cyclic 2-diazo-1,3-dicarbonyl compounds react with diketene in the presence of rhodium(II) salts to give benzofurans as the major isolated products. The formation of intermediate products with exocyclic double bonds which isomerise to benzofurans provides support for the proposed mechanism which involves initial formation of a dioxaspirooctenone by a formal dipolar cycloaddition reaction of a carbenoid to the exocyclic double bond of diketene followed by the loss of carbon dioxide. Acyclic 2-diazo-1,3-dicarbonyl compounds give furans in poor yield.
- Murphy, Paul V.,O'Sullivan, Timothy J.,Kennedy, Bryan D.,Geraghty, Niall W.A.
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p. 2121 - 2126
(2007/10/03)
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- Wood preservative compositions containing dimethylfurancarboxyanilide derivatives
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A dimethylfurancarboxyanilide compound of the formula (I): STR1 wherein R1 and R2 are the same or different and each is hydrogen, (C2 -C6)-alkyl, (C3 -C6)-cycloalkyl, (C3 -C6)-alkenyl, (C2 -C6) alkynyl, (C1 -C3)-halogenoalkyl, (C2 -C6)-alkoxy, (C1 -C6)-alkoxy- (C1 -C6)-alkyl, cyano, substituted amide, (C1 -C6)-alkoxy-carbonyl, benzoyl which is unsubstituted or has 1 to 2 substituents, benzoylamino which is unsubstituted or has 1 to 2 substituents; (C2 -C6)-alkanoylamino, (C3 -C6)-cycloalkylcarbonylamino, benzyl which is unsubstituted or has 1 to 2 substituents, phenyl which is unsubstituted or has 1 to 2 substituents, or (C1 -C6)-alkoxycarbonyl-(C2 -C5)-alkenylene; and R1 and R2 do not both represent hydrogen at the same time. A wood preservative containing the dimethylfurancarboxyanilide compound as an active ingredient. A method of preserving wood by applying the dimethylfurancarboxyanilide compound to wood. A wood preservative composition in which the dimethylfurancarboxyanilide compound is combined with at least one of 3-bromo-2,3-diiodo-2-propenylethylcarbamate, 3-iodo-2-propynylbutylcarbamate and 4-chlorophenyl-3-iodopropargylformal.
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- A NEW SYNTHESIS OF DIHYDROJASMON
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Strictly controlled hydrolysis of 5-methylene-4,5-dihydrofurans 3 allows an efficient approach to 2-acetonyl-1,3-dicarbonyl compounds 4, key intermediates in the synthesis of cyclopentenone derivatives.
- Antonioletti, Roberto,Bonadies, Francesco,Scettri, Arrigo
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p. 233 - 234
(2007/10/02)
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- A CONVENIENT APPROACH TO FURAN DERIVATIVES BY I2-INDUCED CYCLISATION OF 2-ALKENYL SUBSTITUTED 1,3-DICARBONYL COMPOUNDS
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5-iodoalkyl-4,5-dihydrofurans 2, 5-alkylidene-4,5-dihydrofurans 3 and 2,3,5-trisubstituted furans 4 are obtained through a simple sequence, involving, in the key-step, a regio- and stereoselective iodoenoletherification of 2-alkenyl substituted 1,3-dicarbonyl compounds 1.
- Antonioletti, R.,Bonadies, F.,Scettri, A.
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p. 4987 - 4990
(2007/10/02)
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- ALKYLATION OF β-DICARBONYL COMPOUNDS BY 1,2,3-TRIHALOPROPANES AS A METHOD FOR THE PREPARATION OF β-SUBSTITUTED FURANS
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Alkylation of β-dicarbonyl compounds by 1,2,3-trihalides leads to a readily separable mixture of mono- and dialkylation products, and under more rigorous conditions, to 3-substituted 2,4-dimethylfurans.A similar reaction with propargyl bromide leads to furans with a "normal" structure, namely, 2,5-dimethylfurans.
- Akhmedov, Sh. T.,Sadykhov, N. S.,Ismailov, V. M.,Akhundova, M. A.,Sadovaya, N. K.,et al.
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p. 1291 - 1295
(2007/10/02)
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- Lewis acid promoted reactions of ethyl cyanoformate. Reaction with 2,5-dimethylfuran
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Aluminium chloride promoted reaction of 2,5-dimethylfuran with ethyl cyanoformate affords, depending on the experimental conditions, cis and trans ethyl 5-cyano-2,5-dimethyl-2,5-dihydrofuran-2-carboxylates, 3 and 4, ethyl 2,5-dimethylfuran-3-carboxylate 5, 4,8-dicyano-1,2,4,8-tetramethyl-3,9-dioxatricyclo-2,6>decane 6, and ethyl 3-(2,5-dimethyl-3-furyl)-5-cyano-2,5-dimethyltetrahydrofuran-2-carboxylate 7.Structures were elucidated from spectral evidence and chemical transformations.
- McCulloch, Archibald W.,McInnes, A. Gavin,Smith, Donald G.
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p. 1395 - 1402
(2007/10/02)
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- Preparation of 3-carboalkoxy or 3-alkanoyl furans
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A large group of derivatives of 3-furoic acid and 3-furyl ketones can be prepared in high yield by a process which consists of reacting an α,β-unsaturated ketone having either an α-carboalkoxy or α-acyl group with N-bromosuccinimide and thermally cyclizing the resulting bromine containing intermediate.
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