- Synthetic method for medical intermediate 5-nitrofurfural diacetate
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The invention relates to a production technology for 5-nitrofurfural diacetate. A main improvement point of the method is an adding moment and an adding mode of sulfuric acid. Through optimizing, a yield of the 5-nitrofurfural diacetate is improved, and higher purity is kept.
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Paragraph 0018-0066
(2019/03/25)
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- Synthesis, characterization and antiinflammatory activity of chalcone derivatives linked with apocynin and 5-nitrofuran moiety
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The present paper describes the synthesis of some new chalcone derivatives i.e. 1-[3-methoxy-4-(5-nitro-furan-2-ylmethoxy)-phenyl]-3-(substituted phenyl)-propenone derivatives (9A-9K) from furfural and apocynin as starting materials. Claisen-Schmidt reaction of 1-(4-((5-nitrofuran-2-yl)methoxy)-3-methoxyphenyl)ethanone (7) with aromatic aldehydes (8A-K) under solvent free conditions using solid NaOH as catalyst at room temperature resulted in the formation of chalcone derivatives (9A-9K) in 86-96 % yield. These compounds were characterized by 1H NMR, Mass and IR spectroscopy and were evaluated for their anti-inflammatory activity.
- Kumar Reddy,Kathale, Niren E.
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p. 312 - 316
(2018/01/11)
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- Preparation and Characterization of a Small Library of Thermally-Labile End-Caps for Variable-Temperature Triggering of Self-Immolative Polymers
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The reaction between furans and maleimides has increasingly become a method of interest as its reversibility makes it a useful tool for applications ranging from self-healing materials, to self-immolative polymers, to hydrogels for cell culture and for the preparation of bone repair. However, most of these applications have relied on simple monosubstituted furans and simple maleimides and have not extensively evaluated the potential thermal variability inherent in the process that is achievable through simple substrate modification. A small library of cycloadducts suitable for the above applications was prepared, and the temperature dependence of the retro-Diels-Alder processes was determined through in situ 1H NMR analyses complemented by computational calculations. The practical range of the reported systems ranges from 40 to >110 °C. The cycloreversion reactions are more complex than would be expected based on simple trends expected based on frontier molecular orbital analyses of the materials.
- Taimoory, S. Maryamdokht,Sadraei, S. Iraj,Fayoumi, Rose Anne,Nasri, Sarah,Revington, Matthew,Trant, John F.
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supporting information
p. 4427 - 4440
(2018/04/26)
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- Antifungal activity of some nitrofuran incorporated Mannich bases
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A series of 3-substituted-4-(5-nitro-2-furfurylidene) amino-5-mercapto-1,2, 4-triazole Mannich bases (5) have been synthesized. The structures of Schiff bases and Mannich bases were confirmed on the basis of elemental analysis, 1H NMR and mass spectral data. The above compounds were screened for their antifungal activity against C. albicans.
- Shivananda,Shet Prakash
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p. 313 - 316
(2013/09/24)
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- Sulphated zirconia as an eco-friendly catalyst in acylal preparation under solvent-free conditions, acylal deprotection assisted by microwaves, and the synthesis of anhydro-dimers of o-hydroxybenzaldehydes
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A solvent-free approach is described for the regioselective synthesis of acylals (1,1-diacetates) in shorter reaction times and higher yields, compared to conventional methodology using solvents. In the protection reaction of the o-hydroxybenzaldehyde the formation of acetyl compounds and anhydro-dimers was observed. The deprotection reaction involves microwave (MW) exposure of diluted reactants in the presence of solid sulphated zirconia (SZ) catalyst that can be easily recovered and reused. The sulphated zirconia was recycled several times without any loss of activity.
- Palacios-Grijalva, Laura Nadxieli,Cruz-Gonzalez, Deysi Y.,Lomas-Romero, Leticia,Gonzalez-Zamora, Eduardo,Ulibarri, Gerardo,Negron-Silva, Guillermo E.
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experimental part
p. 4065 - 4078
(2010/03/01)
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- Syntheses and spectral properties of unsymmetrically 3,5-disubstituted 2,6-dimethyl-1,4-dihydropyridines
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Unsymmetrically 3,5-disubstituted 4-(5-X-2-furyl)-2,6-dimethyl-1,4-dihydropyridines (where X = H, Br, NO2) have been synthesized and characterized by spectral methods (IR, UV, 1H NMR and MS). The modified Hantzsch method made it possible to prepare the title compounds as well as their N-alkylated derivatives. The paper also describes the N-alkylation of sodium salts of substituted 1,4-dihydropyridines using the phase-transfer catalysis.
- Ilavsky, Dusan,Milata, Viktor
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p. 1233 - 1243
(2007/10/03)
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- Modified Procedure for the Preparation of 5-Nitro-2-furylmethylene Diacetate and Its Use in the Synthesis of Some Novel (5-Nitro-2-furyl)azomethines via 5-Nitro-2-furaldehyde
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A modified two-step procedure for the preparation of 5-nitro-2-furylmethylene diacetate (3) by nitration of 2-furaldehyde (1) or 2-furylmethylene diacetate (4) with acetyl nitrate via 2-acetoxy-5-nitro-2,5-dihydro-2-furylmethylene diacetate (2), or 1,1,5-triacetoxy-2-hydroxy-5-nitro-3-penten (5) and 1,1,5-triacetoxy-2-hydroxy-5-nitro-2,4-pentadiene (6), has been developed.Acid hydrolysis of 3 yields 5-nitro-2-furaldehyde (7) which is used in the carbonylamine condensation with various hydrazines (9-11, 14, 17, 19, 21, 24, 25, 28, 29, 32, 34, 36, 38, 39, 41 and 44-54) prepared by known methods, in order to obtain some novel potentially pharmaceutically active (5-nitro-2-furyl)azomethines.
- Vlaovic, Djordje,Milic, Bozidar Lj.,Mackenzie, Kenneth
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p. 1201 - 1218
(2007/10/02)
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- Nitronium Acetate Adducts of Furan Derivatives
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An improved procedure for the isolation of the main addition products of the reaction between nitronium acetate and furfural diacetate or methyl 2-furoate is described.The kinetics of the deacetylation of the diastereomeric 1,4-adducts in buffer solutions revealed a substantial primary hydrogen isotope effect.Mild acid-induced alcoholysis transformed the adducts into 2,5-dialkoxy-2,5-dihydrofurans.The reaction chemistry of the furan adducts is compared with the solvolytic pathways reported for ipso nitronium acetate adducts formed from alkylbenzenes.
- Balina, Gisela,Kesler, Patricia,Petre, Janet,Pham, Dung,Vollmar, Arnulf
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p. 3811 - 3818
(2007/10/02)
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