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1

Ang, Kiah H., Matthew Cox, Warren D. Lawrance, Rolf Prager, Jason A. Smith, and Warren Staker. "Triplet Lifetimes, Solvent, and Intramolecular Capture of Isoxazolones." Australian Journal of Chemistry 57, no. 1 (2004): 101. http://dx.doi.org/10.1071/ch03140.

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The first step in the photochemical decarboxylation of isoxazolones is the formation of the triplet state of the isoxazolone. We present evidence for the first time from flash laser photolysis of the lifetime of such species, and examples of their capture by solvent and by intramolecular cycloaddition.
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2

Cox, Matthew, Saba Jahangiri, Michael V. Perkins, and Rolf H. Prager. "Some Synthetic Approaches to Glutamate AMPA Receptor Agonists Based on Isoxazolones." Australian Journal of Chemistry 57, no. 7 (2004): 685. http://dx.doi.org/10.1071/ch04041.

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Several approaches to the synthesis of derivatives of the antifungal antibiotic TAN-950A, which is also an agonist of glutamate at hippocampal neurons, are reported. Additions of isoxazolon-4-yl anions to methyleneoxazolidinones were not useful because addition occurred predominantly through N-2. Similarly addition of the isoxazolon-4-yl radicals to model Michael acceptors occurred predominantly through N-2. Racemic analogues of TAN-950A were prepared by reaction of isoxazolone Mannich bases with acetylaminomalonate or addition of β-ketoester anions to dehydroalanines. The best approach to ena
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3

Reddy, Koduru Janardhan, and Kap Duk Lee. "Separation Studies of Pd(II) from Acidic Chloride Solutions of Pt(IV), Ni(II) and Rh(III) by Using 4-Aroyl-3-Phenyl-5-Isoxazolones." E-Journal of Chemistry 9, no. 2 (2012): 756–65. http://dx.doi.org/10.1155/2012/802621.

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This study examined the effect influence of various factors on the extraction of Pd(II) to develop a new liquid-liquid extraction mechanism for the selective separation of palladium(II) from its acidic chloride solutions using 4-aroyl-3-phenyl-5-isoxazolones (HA), such as 3-phenyl-4-(4-fluorobenzoyl)-5- isoxazolone (HFBPI), 3-phenyl-4-benzoyl-5-isoxazolone (HPBI) and 3-phenyl-4- (4-toluoyl)-5-isoxazolone (HTPI). The extraction strength of Pd(II) with HA were in the following order: HFBPI > HPBI > HTPI, which is opposite to that observed with their pKavalues. HPBI was used to separate Pd(
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4

Ciura, Krzesimir, Joanna Fedorowicz, Hanna Kapica, Monika Pastewska, Wiesław Sawicki, and Jarosław Sączewski. "Interaction between Antifungal Isoxazolo[3,4-b]Pyridin 3(1H)-One Derivatives and Human Serum Proteins Analyzed with Biomimetic Chromatography and QSAR Approach." Processes 9, no. 3 (2021): 512. http://dx.doi.org/10.3390/pr9030512.

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The development of effective, nontoxic antifungal agents is one of the most important challenges for medicinal chemistry. A series of isoxazolo [3,4-b]pyridine-3(1H)-one derivatives previously synthesized in our laboratory demonstrated promising antifungal properties. The main goal of this study was to investigate their retention behavior in a human serum proteins-high-performance liquid chromatography (HSA-HPLC) system and explore the molecular mechanism of HSA-isoxazolone interactions using a quantitative structure–retention relationship (QSRR) approach. In order to realize this goal, multip
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5

Rong, Wei, Tian Zhang, Ting Li, and Juan Li. "Theoretical study of rhodium- and cobalt-catalyzed decarboxylative transformations of isoxazolones: origin of product selectivity." Organic Chemistry Frontiers 8, no. 6 (2021): 1257–66. http://dx.doi.org/10.1039/d0qo01498b.

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6

Bustos, Carlos, Elies Molins, Juan-Guillermo Cárcamo, et al. "A family of substituted hydrazonoisoxazolones with potential biological properties." New Journal of Chemistry 40, no. 3 (2016): 2156–67. http://dx.doi.org/10.1039/c5nj02604k.

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7

Ebrahimlo, Ali Reza Molla, Jabbar Khalafy, and Rolf H. Prager. "The Synthesis of Potential DNA Intercalators. 2. Tri- and Tetra-Cyclic Heterocycles." Australian Journal of Chemistry 62, no. 2 (2009): 126. http://dx.doi.org/10.1071/ch08370.

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The reaction of 1,4-dichlorophthalazine and 2,3-dichloroquinoxaline with some isoxazolones gave their mono- and bis-isoxazolinyl derivatives. The base-catalyzed rearrangement of these derivatives afforded the corresponding tri- and tetracyclic heterocycles.
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8

Wentrup, Curt, Maria Wiedenstritt, and Hans-Wilhelm Winter. "Acetylenes from Aldehydes. Preparation of Ethynylphenols and Phenylacetylenes by Flash Vacuum Pyrolysis of Isoxazolones." Australian Journal of Chemistry 68, no. 8 (2015): 1233. http://dx.doi.org/10.1071/ch15234.

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The flash vacuum pyrolysis method of synthesis of acetylenes from aldehydes via isoxazolones is a convenient method for the preparation of a variety of derivatives, including kinetically unstable, sensitive compounds such as the ethynylphenols.
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9

Mahalanabis, Kumar K., S. K. Dutta Chowdhury, Mili Sarkar, and Manisha Misra. "Synthesis of substituted isoxazolones and isoxazoles from cyanoenaminones." Journal of Chemical Research 2006, no. 2 (2006): 78–80. http://dx.doi.org/10.3184/030823406776330864.

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10

Beccalli, Egle M., Tiziana Benincori, and Alessandro Marchesini. "1,3-Oxazin-6-ones from 5(2H)-Isoxazolones." Synthesis 1988, no. 08 (1988): 630–31. http://dx.doi.org/10.1055/s-1988-27660.

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11

Ciura, Krzesimir, Joanna Fedorowicz, Petar Žuvela, et al. "Affinity of Antifungal Isoxazolo[3,4-b]pyridine-3(1H)-Ones to Phospholipids in Immobilized Artificial Membrane (IAM) Chromatography." Molecules 25, no. 20 (2020): 4835. http://dx.doi.org/10.3390/molecules25204835.

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Currently, rapid evaluation of the physicochemical parameters of drug candidates, such as lipophilicity, is in high demand owing to it enabling the approximation of the processes of absorption, distribution, metabolism, and elimination. Although the lipophilicity of drug candidates is determined using the shake flash method (n-octanol/water system) or reversed phase liquid chromatography (RP-LC), more biosimilar alternatives to classical lipophilicity measurement are currently available. One of the alternatives is immobilized artificial membrane (IAM) chromatography. The present study is a con
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12

Ang, KH, RH Prager, and CM Williams. "The Chemistry of 5-Oxodihydroisoxazoles. XII. Trapping of Derived Ketenimines With Lithium Amides and Alkyllithiums." Australian Journal of Chemistry 48, no. 1 (1995): 55. http://dx.doi.org/10.1071/ch9950055.

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Isoxazolones unsubstituted at C3 react with lithium amides or alkyllithiums to give ketenimines . The presence of an ethoxycarbonyl group at C4 allows capture of this species by addition of a second equivalent of the lithiated species to give enolates which can be alkylated in situ. The presence of a phenyl group at C4 gives a ketenimine which reacts intramolecularly in the presence of lithium amides, whereas alkyllithiums undergo addition in synthetically useful processes.
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13

De Castro, Pedro P., Juliana A. Dos Santos, Marcelo M. De Siqueira, Gabriel M. F. Batista, Hélio F. Dos Santos, and Giovanni W. Amarante. "Quantum Chemical-Guided Steglich Rearrangement of Azlactones and Isoxazolones." Journal of Organic Chemistry 84, no. 19 (2019): 12573–82. http://dx.doi.org/10.1021/acs.joc.9b02099.

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14

Koch, Rainer, Hans-Joachim Wollweber, Hans Müller-Starke та Curt Wentrup. "α-Oxo-Iminoxyls of Isoxazolones, Pyrazol­ones and 1,2,3-Triazolone". European Journal of Organic Chemistry 2015, № 23 (2015): 5143–49. http://dx.doi.org/10.1002/ejoc.201500728.

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15

Cox, Matthew, Fariba Heidarizadeh, and Rolf H. Prager. "Flash vacuum pyrolysis of N-alkenylbenzotriazoles and N-alkenylisoxazolones." Australian Journal of Chemistry 53, no. 8 (2000): 665. http://dx.doi.org/10.1071/ch00098.

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The flash vacuum pyrolysis of 1-(2-ethoxycarbonylethenyl)benzotriazole has been reinvestigated, and the processes leading to the formation of ethyl indole-3-carboxylate and 2-ethoxyquinolin-4(1H)-one elucidated. Similar pathways are followed in the flash vacuum pyrolysis of the corresponding benzisoxazolone. Some N-ethenylisoxazolones have been pyrolysed to form pyrroles, but rearrangement of the intermediate carbenes may be observed. Photolysis of the isoxazolones gives carbenes that may be captured by solvent or give pyrroles.
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16

Kvaskoff, David, and Curt Wentrup. "Thioketenes and Iminopropadienethiones RN=C=C=C=S from Isoxazolones." Australian Journal of Chemistry 63, no. 12 (2010): 1694. http://dx.doi.org/10.1071/ch10340.

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Isoxazolones 6 undergo thermal elimination of propene and isopropylthiol to produce thioketenes 7 at 500–600°C under flash vacuum thermolysis conditions. At 700–900°C further fragmentation occurs to produce iminopropadienethiones, RNCCCS 8. In addition, 3-alkylisoxazolones 6d–e rearrange to cyanothioketenes 10d–e. Compounds 7, 8, and 10 were characterized by Ar matrix IR spectroscopy and comparison with density functional theory-calculated spectra. Thioketenes 7 reacted with amines to afford thioamides 11. Reaction of aryliminopropadienethiones 8 with amines caused cyclization to 2-aminoquinol
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17

CHANDE, M. S., and R. M. JOSHI. "ChemInform Abstract: Synthesis of Fused Thiazolo(5,4-d)isoxazoles and a Novel Rearrangement Involving Conversion of 5(4H)-Isoxazolones to 4(5H)-Isoxazolones." ChemInform 28, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199740155.

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18

Mazimba, Ofentse, Kabo Wale, Daniel Loeto, and Tebogo Kwape. "Antioxidant and antimicrobial studies on fused-ring pyrazolones and isoxazolones." Bioorganic & Medicinal Chemistry 22, no. 23 (2014): 6564–69. http://dx.doi.org/10.1016/j.bmc.2014.10.015.

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19

Batra, Sanjay, Mohammad Shamim Akhtar, Manju Seth, and Amiya Prasad Bhaduri. "Chemistry of 5(2H)-isoxazolones: Novel conversion of positional isomers." Journal of Heterocyclic Chemistry 27, no. 2 (1990): 337–42. http://dx.doi.org/10.1002/jhet.5570270242.

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20

Kamlar, Martin, Salil Putatunda, Ivana Císařová, and Jan Veselý. "Enantioselective Synthesis of Spirocyclic Isoxazolones Using a Conia-Ene Type Reaction." Journal of Organic Chemistry 90 (March 5, 2025): 3615–27. https://doi.org/10.5281/zenodo.15095083.

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Abstract Stereoselective synthesis of spirocyclic compounds containing heterocyclic motifs represents a formidable challenge in enantioselective synthesis. Here, we present a cascade reaction between α,β-unsaturated aldehydes and isoxazolones under synergistic catalysis of a chiral secondary amine and a palladium(0) catalyst. This strategy allows access to chiral spiroisoxazolone derivatives with a large substrate scope tolerance and high levels of diastereoselectivity (dr up to 20:1) and enantioselectivity (up to 99% ee). Furthermore, the utility of this methodology is showcased by
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21

Beccalli, Egle M., Alessandro Marchesini, and Tullio Pilati. "Synthesis of heterocyclic ketene N,O-acetals from 5(2H)-isoxazolones." Tetrahedron 53, no. 30 (1997): 10433–40. http://dx.doi.org/10.1016/s0040-4020(97)00654-6.

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22

Flores, Alex F. C., Nilo Zanatta, Adriano Rosa, Sergio Brondani, and Marcos A. P. Martins. "Synthesis of hydroxypyrazoles and 1-methyl-3-isoxazolones via haloform reactions." Tetrahedron Letters 43, no. 28 (2002): 5005–8. http://dx.doi.org/10.1016/s0040-4039(02)00874-2.

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23

NAKAMURA, Koki, Keizo KOYA, and Kozo SATO. "Single electron transfer-triggered ring opening reaction of isoxazolones and its application." Journal of Synthetic Organic Chemistry, Japan 47, no. 7 (1989): 629–35. http://dx.doi.org/10.5059/yukigoseikyokaishi.47.629.

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24

August, Julie, Klaus Klemm, Harold W. Kroto, and David R. M. Walton. "F.t.i.r. study of ynamines and ketenimines produced by thermolysis of substituted isoxazolones." Journal of the Chemical Society, Perkin Transactions 2, no. 11 (1989): 1841. http://dx.doi.org/10.1039/p29890001841.

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25

BATRA, S., and A. P. BHADURI. "ChemInform Abstract: An Account of the Chemistry of 3,4-Disubstituted 5-Isoxazolones." ChemInform 26, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199536302.

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26

ODASHIMA, Tsugikatsu, Seiichi SATOH, Tsugio SATO, and Hajime ISHII. "SOLVENT EXTRACTION OF SOME TERVALENT LANTHANOIDS WITH 4-ACYL-3-PHENYL-5-ISOXAZOLONES." Solvent Extraction and Ion Exchange 13, no. 5 (1995): 845–54. http://dx.doi.org/10.1080/07366299508918306.

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27

Rageh, H. M., S. A. Ibrahim, M. A. Selim, and H. M. Alsoghier. "Spectroscopic and semiempirical investigation of the structural features of hetarylazo-5-isoxazolones tautomerism." Journal of Saudi Chemical Society 21 (January 2017): S467—S474. http://dx.doi.org/10.1016/j.jscs.2015.01.007.

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28

BECCALLI, E. M., A. MARCHESINI, and T. PILATI. "ChemInform Abstract: Synthesis of Heterocyclic Ketene N,O-Acetals from 5(2H)-Isoxazolones." ChemInform 28, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199748049.

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29

Clerici, Francesca, Emanuela Erba, Pierluigi Mornatti, and Pasqualina Trimarco. "Cycloaddition Reactions of 3-Methyloxazolium-5-olates to 4-Arylidene-5(4H)-isoxazolones." Chemische Berichte 122, no. 2 (1989): 295–300. http://dx.doi.org/10.1002/cber.19891220215.

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30

Flores, Alex F. C., Nilo Zanatta, Adriano Rosa, Sergio Brondani, and Marcos A. P. Martins. "ChemInform Abstract: Synthesis of Hydroxypyrazoles and 1-Methyl-3-isoxazolones via Haloform Reactions." ChemInform 33, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.200241121.

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31

Ebrahimlo, Ali Reza Molla, Jabbar Khalafy, Ahmad Poursattar Marjani, and Rolf H. Prager. "The synthesis of potential DNA intercalators. 3†. Triazanaphthalene, tetraaza anthracene and phenanthrene from isoxazolones." Arkivoc 2009, no. 12 (2009): 17–30. http://dx.doi.org/10.3998/ark.5550190.0010.c03.

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32

Christodoulou, Michael S., Sabrina Giofrè, Egle M. Beccalli, Francesca Foschi, and Gianluigi Broggini. "Divergent Conversion of 4-Naphthoquinone-substituted 4H-Isoxazolones to Different Benzo-fused Indole Derivatives." Organic Letters 22, no. 7 (2020): 2735–39. http://dx.doi.org/10.1021/acs.orglett.0c00709.

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33

Jiang, Di, Zheng Xue, Yongjun Li, Huibiao Liu, and Wensheng Yang. "Synthesis of donor–acceptor molecules based on isoxazolones for investigation of their nonlinear optical properties." Journal of Materials Chemistry C 1, no. 36 (2013): 5694. http://dx.doi.org/10.1039/c3tc31228c.

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34

Yu, Wei, Zhengang Liu, Bing Han, et al. "Selective Reduction of the Exocyclic Double Bond of Isoxazolones and Pyrazolones by Hantzsch 1,4-Dihydropyridine." Synlett 2005, no. 10 (2005): 1579–80. http://dx.doi.org/10.1055/s-2005-869860.

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35

Chans, Guillermo M., Elizabeth L. Moyano, and Gloria I. Yranzo. "Novel Synthesis of 2-thienylcarbonyl-cyclohexane-1,3-dione as Building Block for Indazolones and Isoxazolones." Australian Journal of Chemistry 64, no. 5 (2011): 638. http://dx.doi.org/10.1071/ch11015.

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A new synthetic methodology using ultrasonic treatment was applied to the C-acylation of 1,3-cyclohexanedione with thiophene-2-carbonyl chloride to afford 3-hydroxy-2-(2-thienylcarbonyl)cyclohex-2-en-1-one (5). This compound was used as a building block to prepare different bicyclic systems: tetrahydro-4H-indazol-4-ones (7a–c and 9a,b,d), and 6,7-dihydrobenzisoxazole (11) by reaction with different hydrazines and hydroxylamine, respectively. Structural elucidation of all compounds was thoroughly achieved by NMR spectroscopy.
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36

Giovannoni, Maria Paola, Letizia Crocetti, Niccolò Cantini, et al. "New 3‐unsubstituted isoxazolones as potent human neutrophil elastase inhibitors: Synthesis and molecular dynamic simulation." Drug Development Research 81, no. 3 (2019): 338–49. http://dx.doi.org/10.1002/ddr.21625.

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37

RAO, M. H., A. P. R. REDDY, and V. VEERANAGAIAH. "ChemInform Abstract: A Convenient Approach to the Synthesis of Quinoxalines from Isoxazolones and 1,2-Diaminobenzenes." ChemInform 23, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199217200.

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38

Gammill, Ronald B., Sharon A. Nash, Larry T. Bell, and William Watt. "The synthesis and chemistry of functionalized furochromones.4.1 Addition of nitronate anions to 30bromochromone and 6-bromofurochromone. An expedient route to furo(3′,2′:6,7)-benzopyrano(2,3-d)-isoxazolones and chromono(2,3-d)isoxazolones." Tetrahedron Letters 33, no. 8 (1992): 993–96. http://dx.doi.org/10.1016/s0040-4039(00)91842-2.

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39

Sampaio, Ana Beatriz S., Mônica Shigemi S. Mori, Lorena C. Albernaz, Laila S. Espindola, Carlos Eduardo M. Salvador, and Carlos Kleber Z. Andrade. "Continuous Flow Photochemical Synthesis of 3-Methyl-4-arylmethylene Isoxazole-5(4H)-ones through Organic Photoredox Catalysis and Investigation of Their Larvicidal Activity." Catalysts 13, no. 3 (2023): 518. http://dx.doi.org/10.3390/catal13030518.

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Isoxazole-5(4H)-ones are heteropentacycle compounds found in several bioactive molecules with pharmaceutical and agrochemical properties. A well-known multicomponent reaction between β-ketoester, hydroxylamine, and aromatic aldehydes leads to 3-methyl-4-arylmethylene isoxazole-5(4H)-ones, in mild conditions. The initial purpose of this work was to investigate whether the reaction might be induced by light, as described in previous works. Remarkable results were obtained using a high-power lamp, reducing reaction times compared to methodologies that used heating or catalysis. Since there are ma
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40

Milyutin, Constantine Vyacheslavovich, Andrey Nikolaevich Komogortsev, and Boris Valerievich Lichitsky. "Synthesis of 1,2,3-triazoles containing an allomaltol moiety from substituted pyrano[2,3-d]isoxazolones via base-promoted Boulton–Katritzky rearrangement." Beilstein Journal of Organic Chemistry 20 (June 11, 2024): 1334–40. http://dx.doi.org/10.3762/bjoc.20.117.

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For the first time, the interaction of aroyl containing pyrano[2,3-d]isoxazolone derivatives with various hydrazines was studied. It was shown that the considered process includes formation of corresponding hydrazones followed by Boulton–Katritzky rearrangement. As a result, the general method for the synthesis of substituted 1,2,3-triazoles bearing an allomaltol fragment was elaborated. The suggested approach can be applied to various aromatic and heterocyclic hydrazines. At the same time for unsubstituted hydrazine the Boulton–Katritzky recyclization is not implemented. In this case the open
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41

Sekily, Mohamed A. El. "Studies on dehydro-D-erythro-ascorbic acid 2-arylhydrazone 3-oximes: conversion into substituted triazoles and isoxazolones." Journal of Chemical Research 2006, no. 12 (2006): 771–73. http://dx.doi.org/10.3184/030823406780199785.

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42

Gerace, Alessandro, Valentina Masini, Letizia Crocetti, Maria Paola Giovannoni, and Marta Ferraroni. "X-ray structural study of human neutrophil elastase inhibition with a series of azaindoles, azaindazoles and isoxazolones." Journal of Molecular Structure 1274 (February 2023): 134595. http://dx.doi.org/10.1016/j.molstruc.2022.134595.

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43

Valduga, Claudete J., Denise B. Santis, Hugo S. Braibante та Mara E. F. Braibante. "Reactivity ofp-phenyl substituted β-Enamino compounds using K-10/ultrasound.II. Synthesis of isoxazoles and 5-Isoxazolones". Journal of Heterocyclic Chemistry 36, № 2 (1999): 505–8. http://dx.doi.org/10.1002/jhet.5570360229.

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44

Kadam, Hari K., Komal Salkar, Akshata P. Naik, et al. "Silica Supported Synthesis and Quorum Quenching Ability of Isoxazolones Against Both Gram Positive and Gram Negative Bacterial Pathogens." ChemistrySelect 6, no. 42 (2021): 11718–28. http://dx.doi.org/10.1002/slct.202101798.

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45

Beccalli, Egle M., Alessandro Marchesini, and Tullio Pilati. "2-acyl-2,3-dihydro-1,3-oxazin-6-ones and pyrrolo[l,2-a]pyrimidines from 5(2h)-isoxazolones." Tetrahedron 44, no. 19 (1988): 6225–34. http://dx.doi.org/10.1016/s0040-4020(01)89813-6.

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46

Canonne, P., D. Thibeault, and G. Fytas. "Etude des reactions du di(bromomagnesio)-1,4 butane et du di(bromomagnesio)-1,5 pentane sur les isoxazolones-5 encombrees." Tetrahedron 42, no. 15 (1986): 4203–10. http://dx.doi.org/10.1016/s0040-4020(01)87644-4.

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47

Buonomenna, M. G., R. Molinari, and E. Drioli. "Selective mass transfer of iron(III) in supported liquid membrane using highly acidic extractants, 3-phenyl-4-acyl-5-isoxazolones." Desalination 148, no. 1-3 (2002): 257–62. http://dx.doi.org/10.1016/s0011-9164(02)00707-5.

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48

BATRA, S., M. SETH, and A. P. BHADURI. "ChemInform Abstract: Lithium Aluminum Hydride Induced Ring Contraction of 5(2H)- Isoxazolones to Aziridines: Prediction of the Stereochemistry of Products." ChemInform 23, no. 21 (2010): no. http://dx.doi.org/10.1002/chin.199221095.

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49

Ciura, Krzesimir, Joanna Fedorowicz, Filip Andrić, et al. "Lipophilicity Determination of Antifungal Isoxazolo[3,4-b]pyridin-3(1H)-ones and Their N1-Substituted Derivatives with Chromatographic and Computational Methods." Molecules 24, no. 23 (2019): 4311. http://dx.doi.org/10.3390/molecules24234311.

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The lipophilicity of a molecule is a well-recognized as a crucial physicochemical factor that conditions the biological activity of a drug candidate. This study was aimed to evaluate the lipophilicity of isoxazolo[3,4-b]pyridine-3(1H)-ones and their N1-substituted derivatives, which demonstrated pronounced antifungal activities. Several methods, including reversed-phase thin layer chromatography (RP-TLC), reversed phase high-performance liquid chromatography (RP-HPLC), and micellar electrokinetic chromatography (MEKC), were employed. Furthermore, the calculated logP values were estimated using
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50

Reddy, B. Ramachandra, J. Rajesh Kumar, and A. Varada Reddy. "3-phenyl-4-acyl-5-isoxazolones as reagents for liquid-liquid extraction of tetravalent zirconium and hafnium from acidic chloride solutions." Journal of the Brazilian Chemical Society 17, no. 4 (2006): 780–84. http://dx.doi.org/10.1590/s0103-50532006000400021.

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