Awesome Chemistry Experiments For Furan-2,4(3H,5H)-dione

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In the formation of legume-rhizobia symbioses flavonoids released from roots and seeds are best known as inducers of the bacterial nodulation genes that control the synthesis of reciprocal chitolipooligosaccharide signals (Nod factors) to the prospective host plant. However, successful symbiotic development requires the transmission of a variety of other signals from rhizobia to plant roots and flavonoids initiate or mediate the production of most of them. This review considers the wide range of rhizobial responses to these secondary plant metabolites in the early phases of symbiotic interaction, including chemotaxis, growth stimulation, degradation, Nod factor synthesis, protein secretion by type I and III systems, surface polysaccharide production and expression of many new genes and proteins whose functions are only beginning to be analysed. Attention is also drawn to aspects of flavonoid-rhizobia interaction, such as release of compounds from inoculated roots and the reception of nodulation gene inducers by regulatory NodD proteins, that will need to be revisited by researchers if a complete understanding of the molecular dialogue between the partners is to be achieved.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Extracurricular laboratory:new discovery of Furan-2,4(3H,5H)-dione

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Aim and Objective: A novel and convenient transformation for the synthesis of benzodiazepines has been developed via catalytic cyclization reaction using ionic liquid supported on mesoporous silica nanoparticles- imprinted iron metal (Fe-MCM-41-IL) as a recyclable catalyst under mild conditions. Materials and Methods: For preparation of Fe-MCM-41-IL, FeCl3?6H2O was added to a mixture of distilled water, CTAB and NaOH aqueous solution. The tetraethyl orthosilicate was dropped into the solution under stirring. The product was separated, washed, and dried. The solid product was collected and calcined. Then, to a solution of beta-hydroxy-1,2,3-triazole in toluene, 3-chloropropyltrimethoxysilane was added and the mixture was refluxed. The Conc. H2SO4 was added dropwise into the above solution and stirred. For immobilization of IL onto Fe-MCM-41, the solution IL was added to Fe-MCM-41 and was refluxed for the production of the Fe- MCM-41. Following this, benzodiazepines were synthesized using Fe-MCM-41-IL as a catalyst. Results: The Fe-MCM-41-IL was prepared and characterized by a different analysis. The activity of the prepared catalyst as the above described was tested in the model reaction of o-phenyldiamine, tetronic acid, and different aldehydes under room temperature in ethanol solvent. Also, the catalyst could be recovered for five cycles. Conclusion: We developed a novel nanocatalyst for the synthesis of benzodiazepines in excellent yields. Fe- MCM-41-IL as a catalyst has advantages such as: environmental friendliness, reusability and easy recovery of the catalyst using an external magnet.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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We present a modern in silico virtual screening workflow towards novel MurB inhibitors. Namely, the field of antibacterial research is in crucial need of novel lead compounds on new or underexplored therapeutic targets such as MurB. We identified three structurally distinct compounds that indicated promising micromolar inhibitory activity on E. coli MurB. All three compounds did not display cytotoxicity on HepG2 cell line, but also did not possess in vitro antimicrobial activity against S. aureus and E. coli. After the second biological evaluation using radio-labelled substrates in a MurA-MurB coupled test, only marginal inhibitory potency could be reproduced on MurB. As no compound in the series was able to significantly decrease the residual activity of the enzyme, we decided to report the complete inactive compound set to be used as decoys.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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A series of five-membered lactones (both saturated and unsaturated) and a lactam were analysed by electrospray ionisation tandem (ESI-MS/MS) and sequential mass spectrometry (ESI-MSn). It was observed that the main fragment ions were derived from neutral losses of CO and/or H2O (NH3 for the lactam). The fragmentation pathways followed are rationalised in terms of the resulting carbocation stability and the energy of the possible fragment ions, calculated by the CBS-Q composite method.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Discovery of Furan-2,4(3H,5H)-dione

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The synthesis of the benzo[f]furo[3,4-c] [2,7]naphthyridines 15 and 17, the thieno[2,3-c] [2,7]naphthyridines 21 as well as the pyrimido[5,4-c]quinoline 25 is described. These compounds and the structurally related diaza- and triaza-phenanthrenes 3-8 were studied concerning the inhibition of the soybean lipoxigenase. Among these compounds 8 showed the best activity (IC50 = 36 mumol/l).

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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(Chemical Equation Presented) A series of 4-aryl-3-methyl-1-phenyl-7H- furo[3,4-e]pyrazolo[3,4-b]pyridine-5-ones were synthesized via the three-component reaction of an aldehyde, 5-amino-3-methyl-1-phenyl-1H-pyrazole and tetronic acid in aqueous media in the presence of triethylbenzylammonium chloride (TEBAC). This method has the advantages of easier work-up, mild reaction conditions, high yields, and an environmentally benign procedure.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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A series of new N-substituted furo[3,4-b]quinoline derivatives were synthesized via a three-component reaction of an aldehyde, an enamineone and tetronic acid in glacial acetic acid under microwave irradiation without a catalyst. This new protocol has the advantages of shorter time, higher yields, lower cost and broader substrate scope, as well as easier operation.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description:

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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An approach was developed to the synthesis of stable in metabolism 3,7-interphenylene 3,10-dioxa-13-aza-and 3,11-dioxa-13-azaprostanoids, and also 9-oxa-7-azaprostanoids with interphenylene and terminal phenyl fragments in the omega-chain based on 3-(alkoxybenzylidene)-and 3-(3-phenylallylidene) tetrahydrofuran-2,4-diones obtained by Knoevenagel condensation of tetronic acid with alkoxy-substituted aromatic aldehydes and cinnamic aldehyde.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

A new application about Furan-2,4(3H,5H)-dione

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The catalyst-free domino reaction of ethyl 4-hydroxyalkyl-2-ynoate and N-heteroaryl-methyl-N-2, 2-difluoroethan-1-amine was developed, and used to synthesize 4-(N-(2, 2-difluoroethyl)(N-heteroarylmethyl)amino)-5, 5-disubstitutedfuran-2(5H)-one in methanol under the reflux condition with yields of 39%~83%. Their structures were characterized by 1H NMR, 13C NMR, and HR-ESI-MS data, further confirmed by the X-ray crystal diffraction of 3-chloro-4-((N-2, 2-difluoroethyl)(N-pyrimidin-5-ylmethyl)amino)-5, 5-spiro(4-methoxycyclohexyl)furan-2(5H)-one (8). The bioassay results showed that 4-((N-2, 2-difluoroethyl)(N-6-chloropyridin-3-ylmethyl)amino)-5, 5-dimethylfuran-2(5H)-one (3a) and 4-((N-2, 2-difluoroethyl)(N-6-fluoropyridin-3-ylmethyl)-amino)-5, 5-dimethylfuran-2(5H)-one (3c) exhibit 100% mortality against Myzus persicae at the concentration of 600 mug?mL-1, respectively.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem