- Synthesis of methyl furan-2-carboxylate and dimethyl furan-2,5- dicarboxylate by copper-catalyzed reactions of furans with CCl4 and MeOH
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Methyl furan-2-carboxylate and dimethyl furan-2,5-dicarboxylate were obtained in high yields by copper-catalyzed reactions of furan, furfural, 2-acetylfuran, and furan-2-carboxylic acid with CCl4 and MeOH.
- Khusnutdinov,Bayguzina,Mukminov
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- Method for producing furandicarboxylic acid and derivatives thereof from furfural
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The invention discloses a method for producing furandicarboxylic acid and derivatives thereof from furfural. The method comprises the following steps: furfural is reduced to 2-methylfuran under the hydrogen condition; acetylation reaction is carried out on 2-methylfuran to obtain 5-methyl-2-acetylfuran; 5-methyl-2-acety furan reacts with ester to obtain methyl 5-methyl-2-furanformate, methyl 5-methyl-2-furanformate is oxidized into monomethyl 2,5-furandicarboxylate under the oxygen condition, and monomethyl 2,5-furandicarboxylate is hydrolyzed into monomethyl 2,5-furandicarboxylate or furtheresterified with methyl alcohol to generate dimethyl 2,5-furandicarboxylate. The cheap five-carbon furan compound furfural is used as a raw material, and the 2 5-furandicarboxylic acid and the derivatives thereof are prepared by a strategy of increasing a carbon chain, so that the cost of the raw material is greatly reduced. The product provided by the invention has high purity and can be directlyused as a polymerization monomer of PET polyester.
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Paragraph 0034; 0044-0046
(2020/06/05)
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- A tunable precious metal-free system for selective oxidative esterification of biobased 5-(hydroxymethyl)furfural
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Oxidative esterification of biomass-derived 5-(hydroxymethyl) furfural (HMF) and furfural and their derivatives has been performed using a simple MnO2/NaCN system. The developed method allows the selective one-pot transformation of HMF to dimethyl furan-2,5-dicarboxylate (FDME) in 83% isolated yield without the formation of a free acid. Simplification of FDME production provides the missing link for manufacturing sustainable value-added materials from biomass. Addition of water to the oxidative system allows fine-tuning of reaction selectivity to obtain the previously difficult-to-access pure methyl 5-(hydroxylmethyl)furan-2-carboxylate in one step directly from the unprotected HMF without chromatographic separation.
- Kozlov, Kirill S.,Romashov, Leonid V.,Ananikov, Valentine P.
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supporting information
p. 3464 - 3468
(2019/06/24)
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- ARYLDIAZEPINE DERIVATIVES AS RSV INHIBITORS
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The present invention discloses compounds of Formula (I), and pharmaceutically acceptable salts, esters, or prodrugs thereof, which inhibit Respiratory Syncytial Virus (RSV). The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from RSV infection. The invention also relates to methods of treating an RSV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.
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Page/Page column 60
(2019/01/06)
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- Catalyst-controlled regiodivergent C-H borylation of multifunctionalized heteroarenes by using iridium complexes
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The regiodivergent C-H borylation of 2,5-disubstituted heteroarenes with bis(pinacolato)diboron was achieved by using iridium catalysts formed in situ from [Ir(OMe)(cod)]2/dtbpy (cod=1,5-cyclooctadiene, dtbpy: 4,4′-di-tert-butyl-2,2′-bipyridine) or [Ir(OMe)(cod)]2/2 AsPh3. When [Ir(OMe)(cod)]2/dtbpy was used as the catalyst, borylation at the 4-position proceeded selectively to afford 4-borylated products in high yields (dtbpy system A). The regioselectivity changed when the [Ir(OMe)(cod)]2/2 AsPh3 catalyst was used; 3-borylated products were obtained in high yields with high regioselectivity (AsPh3 system B). The regioselectivity of borylation was easily controlled by changing the ligands. This reaction was used in the syntheses of two different bioactive compound analogues by using the same starting material. Minor adjustments, major differences: The regiodivergent C-H borylation of 2,5-disubstituted heteroarenes with bis(pinacolato)diboron was achieved by using iridium catalysts formed in situ from [Ir(OMe)(cod)]2/dtbpy (cod=1,5-cyclooctadiene, dtbpy: 4,4'-di-tert-butyl-2,2'-bipyridine) or [Ir(OMe)(cod)]2/2 AsPh3 (see scheme).
- Sasaki, Ikuo,Taguchi, Jumpei,Hiraki, Shotaro,Ito, Hajime,Ishiyama, Tatsuo
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supporting information
p. 9236 - 9241
(2015/06/16)
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- Cross-coupling reaction with lithium methyltriolborate
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We newly developed lithium methyltriolborate as an air-stable white solid that is convenient to handle. The good performance of this triolborate for metal-catalyzed bond-forming reactions was demonstrated in palladium-catalyzed cross-coupling reactions wi
- Yamamoto, Yasunori,Ikizakura, Kazuya,Ito, Hajime,Miyaura, Norio
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p. 430 - 439
(2013/03/13)
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- The scent of bacteria: Headspace analysis for the discovery of natural products
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Volatile compounds released by 50 bacterial strains, 45 of them actinobacteria in addition to three chloroflexi and two myxobacteria, have been collected by use of a closed-loop stripping apparatus, and the obtained headspace extracts have been analyzed by GC-MS. Excluding terpenes that have recently been published elsewhere, 254 compounds from all kinds of compound classes have been identified. For unambiguous compound identification several reference compounds have been synthesized. Among the detected volatiles 12 new natural products have been found, in addition to mellein, which was released by Saccharopolyspora erythraea. The iterative PKS for this compound has recently been identified by in vitro experiments, but mellein production in S. erythraea has never been reported before. These examples demonstrate that headspace analysis is an important tool for the discovery of natural products that may be overlooked using conventional techniques. The method is also useful for feeding experiments with isotopically labeled precursors and was applied to investigate the biosynthesis of the unusual nitrogen compound 1-nitro-2-methylpropane, which arises from valine. Furthermore, several streptomycetes emitted compounds that were previously recognized as insect pheromones, thus questioning if bacterial symbionts are involved in insect communication.
- Citron, Christian A.,Rabe, Patrick,Dickschat, Jeroen S.
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supporting information
p. 1765 - 1776
(2013/01/15)
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- Cephalosporins and homologues, preparations and pharmaceutical compositions
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β-Lactam antibiotics of formula (I) or a salt thereof, wherein R1 is hydrogen, methoxy or formamido; R2 is an acyl group; CO2 R3 is a carboxy group or a carboxylate anion, or R3 is a readily removable
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- AMBERLYST 15: A PRACTICAL, MILD AND SELECTIVE CATALYST FOR METHYL ESTERIFICATON OF CARBOXYLIC ACIDS
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Mild and selective methyl esterification of carboxylic acids are realized using Amberlyst 15 as acid catalyst in methanol.No racemization, epimerization or ketalization products have been observed with this method.Excellent results are obtained in the esterifications of bile acids.
- Petrini, Marino,Ballini, Roberto,Marcantoni, Enrico
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p. 847 - 854
(2007/10/02)
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- Oxidation of 2,4-Alkadienoic Esters with Selenium Dioxide. A New Synthesis of Furans and Selenophenes
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Direct oxidation of 2,4-alkadienoic esters with selenium dioxide gave 5-alkyl-2-furancarboxylic esters along with 5-alkyl-2-selenophenecarboxylic esters.Ethyl 5-methylfurancarboxylate was converted to 5-hydroxymethyl-2-furancarbaldehyde, a component of honey, via ethyl 5-bromomethyl-2-furancarboxylate (5) in good yield.The compound 5 was converted to (5-ethoxycarbonyl-2-furyl)methyl dimethylditiocarbamate possessing fungicidal activity.Reaction of triphenylphosphonium salt of 5 with nonanal gave ethyl 5-(1-decenyl)-2-furancarboxylate (E/Z=88:12) in 86percent yield.Ethyl 5-methyl-2-selenophenecarboxylate was also converted to ethyl-5- (1-decenyl)-2-selenophenecarboxylate (E/Z=7:3) in 30percent total yield.
- Tsuboi, Sadao,Mimura, Shigetoshi,Ono, Shin-ichiro,Watanabe, Kenji,Takeda, Akira
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p. 1807 - 1812
(2007/10/02)
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- A NOVEL SYNTHESIS OF 2,5-DISUBSTITUTED FURANS AND SELENOPHENES VIA THE OXIDATION OF 2,4-ALKADIENOIC ESTERS WITH SeO2
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A new synthesis of 5-alkyl-2-furancarboxylates and 5-alkyl-2-selenophenecarboxylates via the direct oxidation of 2,4-alkadienoic esters with selenium dioxide is described.
- Tsuboi, Sadao,Watanabe, Kenji,Mimura, Shigetoshi,Takeda, Akira
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p. 2643 - 2644
(2007/10/02)
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- PHOTOCHEMISTRY OF 3,6-DIHYDRO-1,2-OXAZINES: A VERSATILE ROUTE TO SUBSTITUTED PYRROLES
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A high yield pyrrole synthesis which employs a sequence of cycloaddition, photoextrusion of H2O and Birch reduction has been developed.
- Givens, R. S.,Choo, D. J.,Merchant, S. N.,Stitt, R. P.,Matuszewski, B.
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p. 1327 - 1330
(2007/10/02)
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- The Reaction on 2-Methylfuran with Methyl Acrylate Unusual Formation of 1,2'-Bis(5-methyl-2-furyl)ethane and Methyl 3,3'-Bis(5-methyl-2-furyl)propionate
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The reaction of 2-methylfuran with methyl acrylate in the presence of Pd(OAc)2 gave unusual products such as 1,1'-bis(5-methyl-2-furyl)ethane (22percent) and methyl 3,3'-bis(5-methyl-2-furyl)propionate (10percent) along with the usual aromatic substitution product.This is a marked contrast to the reaction of furan with olefins.
- Maruyama, Osamu,Fujiwara, Yuzo,Taniguchi, Hiroshi
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p. 2851 - 2852
(2007/10/02)
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