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A series of novel 3-acetyl-4-hydrazinyl-5,5-disubstitutedtetronic acid and (E/Z)-3-(1-hydrazinylethyli-dene)-5,5-disubstitutedfuran-2,4-dione derivatives were designed and synthesized, and four methyl 5-methyl pyrazole-4-carboxylate were obtained unexpectedly. Their structures were confirmed by high-resolution mass spectrum (HR-ESI-MS), 1H NMR, 13C NMR spectral data and X-ray diffraction. The bioassay results of the hydrazinyl compounds along with the amino analogues indicated that some compounds exhibited moderate to excellent fungicidal activities against phytopathagens. For example, compounds 5G, 5H, 5I and 5i showed 100% in vivo control efficacy against Colletotrichum lagenarium, and compound 5G also exhibited 100% in vivo control efficacy against Erysiphe graminis, Puccinia polysora and Colletotrichum lagenarium at 400 mug/mL. Compounds 5b, 5E and 6F showed 100% mortality against Plutella xylostella, compounds 6A, 6g and 6H exhibited 100% mortality against Myzus persicae, and compound 6b showed 100% mortality against Tetranychus cinnabarinus at 600 mug/mL. The 5,5-spiro cyclohexyl moiety significantly improved the fungicidal activity of the tetronic acid derivatives, and the introduction of the substituted hydrazino group to the furan-2,4-dione skeleton led to higher insecticidal and acaricidal activities. 5G and 5i were found to have the most potential to be further modified for searching new fungicide as the lead compounds.

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

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Infrared and FT-Raman spectra of both deuterated and undeuterated tetronic acid have been examined.The enol form predominates in the solid form, but some keto form is apparent in the spectra.Reported here are the tentative assignments for all bands observed from 4000 to 200 cm-1.Group frequencies obtained by comparing the spectral data acquired with vibrational assignments of similar compounds by other investigators were used to aid the assignment.The spectra are consistent with CS point group, indicating the structure of tetronic acid to be planar in the solid state.

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

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2,4(3H,5H)-Furandione, 1, condenses with heteroaromatic aldehydes in the presence of concentrated hydrochloric acid to yield 3-(heteroarylmethylene)-2,4(3H,5H)-furandiones, 4.The condensation of 1 with acid sensitive aldehydes, including 2-furanacroleine and N-methylpyrrole-2-carboxaldehyde proceeded well with 1 as the sole proton source.The E/Z ratio of type 4 compounds was determined by 1H-nmr spectroscopy.

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Tetrahydrofuran – Wikipedia,
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The synthesis of 2-(3-(4-(dimethylamino)phenyl)-2-oxoindolin-3-yl)-1H- indene-1,3(2H)-diones as new unsymmetrical oxindoles via a Friedel-Crafts type three-component reaction of 1,3-indandion, N,N-dimethylaniline and isatins in ethanol in the presence of LiClO4 is reported.

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Tetrahydrofuran – Wikipedia,
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Covering: selected examples in the past three decades (up to 2018) The challenging structures and often potent biological activities of naturally occurring macrocycles have attracted much attention among the synthetic community. In a typical retrosynthetic disconnection, commonly used macrocyclization tactics, including macrolactonization, macrolactamization, ring-closing metathesis, olefination, and metal-mediated cross-coupling reactions, are invariably based on linear substrates in which all of the stereogenic centers have already been set forth. Macrocyclizations with the simultaneous installation of the requisite stereogenic centers can be advantageous with respect to a broader substrate spectrum as well as a usually higher overall synthetic efficiency. However, achieving predictably high levels of stereocontrol remains a formidable challenge. In this review, we discuss representative examples of those “nonclassic” macrocyclization strategies in the context of natural product total synthesis. Different types of macrocycle-forming methods are summarized, with a particular focus on the sense of diastereoinduction imparted through the transition-state macrocyclic ring architecture (?12-membered) or the catalyst.

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

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Abstract: An efficient and green reaction of isatins, 3-amino-1-phenyl-2-pyrazolin-5-one (3-amine-1H-pyrazole), and beta-diketone in aqueous medium in the presence of PEG ?SO 3H is reported, and a series of novel spirocompounds was obtained with high yields. The advantages of this reaction were simple procedure, moderate reaction conditions, and wide range of substrates. More importantly, the catalyst PEG ?SO 3H could be recovered for reuse up to five times. Graphical Abstract: [Figure not available: see fulltext.].

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

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An amino acid-catalyzed three-component reductive coupling protocol has been developed for the selective high-yielding synthesis of nearly fifty examples of propargylated cyclic/acyclic systems from the various propargyl aldehydes, cyclic/acyclic CH acids, and Hantzsch ester under ambient conditions. It is an economical, efficient, catalytic, metal-free protocol for the quick gram-scale synthesis of propargylated cyclic/acyclic compounds, and many of these coupling compounds were purified by a simple precipitation-filtration technique instead of column chromatography. Functionally rich propargylated cyclic-1,3-diketones were specifically transformed into dihydropyrans found in natural products and drugs through an annulative etherification reaction by using Lewis-acid (AgOTf) catalysis. Further, we developed the C-methylation reactions on propargylated cyclic-1,3-diketones, which are prolific synthons in natural products and medicinal chemistry.

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Tetrahydrofuran – Wikipedia,
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Microorganisms are found everywhere, and they are closely associated with plants. Because the establishment of any plant-microbe association involves chemical communication, understanding crosstalk processes is fundamental to defining the type of relationship. Although several metabolites from plants and microbes have been fully characterized, their roles in the chemical interplay between these partners are not well understood in most cases, and they require further investigation. In this review, we describe different plant-microbe associations from colonization to microbial establishment processes in plants along with future prospects, including agricultural benefits.

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

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A microwave-assisted regioselective synthesis of 3-functionalized indole derivatives via a three-component domino reaction of anilines, arylglyoxal monohydrates, and cyclic 1,3-dicarbonyl compounds is described. The main advantages of this protocol are short reaction times, practical simplicity, its metal-free nature, the availability of starting materials, green solvents, and high regioselectivity.

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

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Antimicrobial resistance constitutes a global health problem, while the discovery and development of novel antibiotics is stagnating. Methicillin-resistant Staphylococcus aureus, responsible for the establishment of recalcitrant, biofilm-related infections, is a well-known and notorious example of a highly resistant micro-organism. Since resistance development is unavoidable with conventional antibiotics that target bacterial viability, it is vital to develop alternative treatment options on top. Strategies aimed at more subtle manipulation of bacterial behavior have recently attracted attention. Here, we provide a literature overview of several small-molecule potentiators for antibiotics, identified for the treatment of Staphylococcus aureus infection. Typically, these potentiators are not bactericidal by themselves and function by reversing resistance mechanisms, by attenuating Staphylococcus aureus virulence, and/or by interfering with quorum sensing.

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