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Crystal structure and Hirshfeld surface analysis of (Z)-4-(4-hydroxybenzylidene)-3-methylisoxazol-5(4H)-one

The title compound, C11H9NO3, contains an isoxazole and a hydroxybenzylidene ring, which are inclined to each another by 3.18 (8). There is an intramolecular C – H?O contact forming an S(7) ring. In the crystal, molecules stack head-to-tail in columns along the b-axis direction, linked by offset pi-pi interactions [intercentroid distances of 3.676 (1) and 3.723 (1) A]. The columns are linked by O – H?O and O – H?N hydrogen bonds, forming layers parallel to the ab plane. The layers are linked by C – H?O hydrogen bonds, forming a supramolecular three-dimensional framework. An analysis of the Hirshfeld surfaces points to the importance of the O – H?O and O – H?N hydrogen bonding in the packing mechanism of the crystal structure.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Facile Synthesis of Fluorinated Isoxazoles via Consecutive Double C-F Bond Cleavage

Fluorinated heterocycles represent a ubiquitous structural motif found in numerous pharmaceuticals, agrochemicals, and functional materials. This is especially true for fluorine-containing five-membered heteroaromatic compounds that have been widely investigated in various fields for a long time. In this context, fluorinated isoxazoles have emerged as valuable scaffolds owing to their diverse biological properties. Among various approaches that have been developed for the synthesis and functionalization of isoxazoles, efficient and modular route to fluorine-substituted isoxazoles are still limited. Traditional methods include the condensation of 2-fluoro-1,3-dicarbonyl derivatives with hydroxylamine, Au-catalyzed fluorocyclization of 2-alkyne O-methyloximes, and direct fluorination of isoxazoles. However, the wide applicability of these approaches often suffers from low chemical yields, harsh reaction conditions, and limited substrate scope. Herein, we describe a one-pot protocol for the construction of fluorinated isoxazoles from CF3-containing precursors with hydroxylammonium chloride. Typical features of this reaction include mild conditions, simple operations, and good functional group compatibility. This method provides facile access to a series of 3-F-5-aryl-isoxazoles in moderate to good yields from easily available alpha-CF3-beta-keto esters. Moreover, further synthetic transformations of obtained isoxazoles to important bio-active molecular derivatives have also been demonstrated. A representative procedure for this reaction is as following: alpha-CF3-beta-keto ester 1 (0.2 mmol, 1.0 equiv.), HONH2?HCl (46 mg, 0.66 mmol), pyridine (71 muL, 0.88 mmol), and CH3CN (3.0 mL) were added into an oven-dried vial equipped with a magnetic stir bar. The mixture was stirred at 75 ? for 12 h and monitored by thin-layer chromatography (TLC). After completion, 10 mL of water was added and the mixture was extracted with EtOAc for three times. The combined organic layers were washed with saturated NaCl and dried over Na2SO4. The mixture was evaporated under reduced pressure and residue was purified by flash chromatography on silica gel eluting with petroleum ether/ethyl acetate (V:V=30:1) to afford the 3-F-5-aryl-isoxazole 2.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Synthesis and biological evaluation of ferrocene-based cannabinoid receptor 2 ligands

Ferrocene analogs of known fatty acid amide hydrolase inhibitors and CB2 ligands have been synthesized and characterized spectroscopically and crystallographically. The resulting bio-organometallic isoxazoles were assayed for their effects on CB1 and CB2 receptors as well as on fatty acid amide hydrolase. None had any fatty acid amide hydrolase activity but compound 3, 5-(2-(pentyloxy)phenyl)-N-ferrocenylisoxazole-3-carboxamide, was found to be a potent CB2 ligand (Ki = 32.5 nM).

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Synthesis and biological evaluation of novel 1,8-Naphthyridines containing pyrazolinone, pyrazole, isoxazolinone, isoxazole and pyrimidine-2-ones

Diazonium salt of 2-(p-aminophenyl)-1,8-naphthyridine (I) was coupled with active methylene compounds to afford the hydrazono-1,8-napthyridinyl (III-V) and azo(VI) derivatives. Hydrazono ethyl acetoacetate (III) and ethyl cyanoacetate (IV) derivatives on treatment with hydrazine and substituted hydrazine’s were later reacted with hydroxylamine HCl in the presence of ethanol followed by cyclization to afford pyrazolinone (IIIa-e) and (IVa-e) and isoxazolinones (VII and IX). Hydrazono acetyl acetone (V) and azo dibenzoyl methane (VI) derivatives on treatment with hydrazine and substituted hydrazines, hydroxylamine HCl and with urea in the presence of ethanol followed by cylization resulted in the formation of pyrazoles (Va-e) and (VIa-e), isoxazole (IX and XI) and substituted pyrimidine-2-ones (X and XII). All the newly synthesized compounds were screened for their in-vitro antibacterial activity and antifungal activity by Agar cup-plate method and Serial dilution methods. In Agar cup plate method the Compounds IIId, IVd, VId showed Impressive antibacterial and antifungal activity. In Serial dilution method the compounds Vd and VId showed excellent antibacterial activity against B.Subtilis with an MIC of 7.8 and mug/ml where as the compounds IVd, Vd showed very good antifungal activity against A.niger and C.albicans with MIC value of 7.8 and mug/ml and 15.6 and mug/ml. We found that the activity was due to presence of chloro group at the para position of phenyl ring of Pyrazolinone and pyrazole and also the presence of methyl group and amino group at the 3rd position, hydrazono and azo (N=N) group at 4th of the pyrazolinone (IIId, IVd) and pyrazole (Vd) ring are contributing to the antimicrobial activity.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

The four-membered oxetane ring has been increasingly exploited for its contrasting behaviors: its influence on physicochemical properties as a stable motif in medicinal chemistry and its propensity to undergo ring-opening reactions as a synthetic intermediate. These applications have driven numerous studies into the synthesis of new oxetane derivatives. This review takes an overview of the literature for the synthesis of oxetane derivatives, concentrating on advances in the last five years up to the end of 2015. These methods are clustered by strategies for preparation of the ring and further derivatization of preformed oxetane-containing building blocks. Examples of the use of oxetanes in medicinal chemistry are reported, including a collation of oxetane derivatives appearing in recent patents for medicinal chemistry applications. Finally, examples of oxetane derivatives in ring-opening and ring-expansion reactions are described.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Synthesis of New Sulfoximine-Tethered Alkynones and Further Extension towards Metal-Free Synthesis of Pyrimidines, Amino Pyrimidines, Pyrazoles and Isoxazoles

A metal free and divergent synthetic method has been successfully developed for the synthesis of sulfoximine tethered pyrimidines, amino pyrimidines, pyrazoles and isoxazoles. Two key sulfoximine tethered alkynone intermediates ((tert-butyldiphenylsilyl)imino)(2-oxo-4-phenylbut-3-yn-1-yl)(phenyl)-lambda6-sulfanone (3 a) and ((tert-butyldiphenylsilyl)imino)(2-oxopent-3-yn-1-yl)(phenyl)-lambda6-sulfanone (3 b), have been reported for the first time and were used as the common building blocks to construct these heterocycles. Good functional group tolerability was observed and the products were isolated in excellent yield.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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A review on ?Drugs containing imidazoles and triazole heterocyclic ring in antifungal therapy?

Writing investigation of different exploration papers and different distributions gives definite work on science of the imidazole,triazole and its different pharmacological activities on different sorts of parasitic contaminations. Imidazole is a substance which is being combined in a number of its subordinate structure from recent years. In the most recent couple of decades,the science of imidazole,triazole and their combined heterocyclic subordinates has gotten significant consideration attributable to their manufactured and viable natural exercises,for example,mitigating,CNS stimulants narcotics,hostile to nervousness,antimicrobial specialists and against mycotic action,for example,fluconazole,intraconazole,voriconazole and so on. Triazole ring framework and imidazole ring framework have pulled in a persistently developing enthusiasm of manufactured natural scientific experts and those managing the therapeutic mixes because of its adaptable potential to interface with organic frameworks. Amid the previous three decades,the frequencies and sorts of systemic parasitic diseases have expanded significantly in patients endured with tumors,immuno insufficiency or invulnerable concealment. The new antifungal operator gives promising movement,obtrusive parasitic contaminations,positioning close by bacterial diseases. The triazole and imidazole mixes have an extensive variety of natural exercises and are particularly engaged for antifungal conduct. The principle center was on the techniques which manage the easy and advantageous combination.

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Synthesis and Cytotoxicity of 28-Oxo-Allobetulone Derivatives

28-Oxo-allobetulone derivatives that were newly synthesized or prepared earlier by modification of ring A (3- and 4-pyridylidene, furfurylidene, azepane, lactam, quinolone, spiroindole, pyrazole, isoxazole, and tetraoxane derivatives) and 3beta,19beta,28-oleantriol were tested in vitro for cytotoxicity against 60 cell lines of 9 human tumor types. Melanoma SK-MEL-5 and CNS SNB-75 cancer cells died in the presence of 3- or 4-pyridylidene derivatives of 28-oxo-allobetulone. 3beta,19beta,28-Oleantriol possessed selective cytotoxicity against CNS cancer cell line SNB-75.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Gold-catalyzed [4+3]- and [4+2]-annulations of 3-en-1-ynamides with isoxazoles: Via novel 6pi-electrocyclizations of 3-azahepta trienyl cations

New gold-catalyzed [4+3]-annulations of 3-en-1-ynamides with isoxazoles afford 4H-azepines efficiently; this process involves 6pi electrocyclizations of gold-stabilized 3-azaheptatrienyl cations. In the presence of Zn(OTf)2, the resulting 4H-azepines undergo skeletal rearrangement to furnish substituted pyridine derivatives. We subsequently develop new catalytic [4+2]-annulations between the same 3-en-1-ynamides and isoxazoles to deliver substituted pyridine products using Au(i)/Zn(ii) catalysts. This work reports the first success of the 6pi electrocyclizations of heptatrienyl cations that are unprecedented in literature reports.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Characterization of free radicals in clathrate hydrates of pyrrole, thiophene, and isoxazole by muon spin spectroscopy

Gas hydrates have long been of interest to the petrochemical industry, but there has been growing interest in potential applications for carbon dioxide sequestration and hydrogen storage. This has prompted many fundamental studies of structure and host-guest interactions, but there has been relatively little investigation of chemical reactions of the guest molecules. In previous work, we have shown that it is possible to use muon spin spectroscopy to characterize H atom like muonium and muoniated free radicals formed in clathrate hydrates. Muonium (Mu) forms in clathrate hydrates of cyclopentane and tetrahydrofuran, whereas furan and its dihydro derivatives form radicals. The current work extends studies to clathrates hydrates of other five-membered heterocycles: thiophene, pyrrole, and isoxazole. All form structure II hydrates. In addition to the clathrates, pure liquid samples of the heterocycles were studied to aid in the assignment of radical signals and for comparison with the enclathrated radicals. Similar to furan, two distinct radicals are formed when Mu reacts with thiophene and pyrrole. However, only one muoniated radical was detected from isoxazole. Muon, proton, and nitrogen hyperfine constants were determined and compared with values predicted by DFT calculations to aid the structure assignments. The results show that Mu adds preferentially to the carbon adjacent to the heteroatom in thiophene and pyrrole and to the carbon adjacent to oxygen in isoxazole. The same radicals are formed in clathrates, but the spectra have broader signals, suggesting slower tumbling. Furthermore, additional signals in the avoided level-crossing spectra indicate anisotropy consistent with restricted motion of the radicals in the clathrate cages.

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Reference£º
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem