FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2075737008> ?p ?o ?g. }

• W2075737008 endingPage "M573" @default.
• W2075737008 startingPage "M573" @default.
• W2075737008 abstract "first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing:    Column Width:    Background: Open AccessShort Note 3-(1-Phenyl-1H-pyrazol-4-yl)-1,2-benzisoxazole 2-oxide by Antigoni Kotali Laboratory of Organic Chemistry, Department of Chemical Engineering, College of Engineering, University of Thessaloniki, Thessaloniki 54006, Greece Molbank 2008, 2008(2), M573; https://doi.org/10.3390/M573 Received: 24 April 2007 / Revised: 8 August 2008 / Accepted: 18 August 2008 / Published: 24 August 2008 Download Download PDF Download PDF with Cover Download XML Download Epub Download Supplementary Material Versions Notes Keywords: (2-hydroxyphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone oxime; diacetoxy iodobenzene; oxidation; cyclisation It is well known that both isoxazole ring as well as pyrazole ring possess various biological activities and they both show interesting antimicrobial activity [1,2,3]. Therefore, it is not unreasonable to believe that a molecule bearing both moieties would possible show combined activity. Having this in mind we designed the synthesis of 3-(1-phenyl-1H-pyrazol-4-yl)-1,2-benzisoxazole 2-oxide as shown below. Nitrogen derivatives of o-hydroxyaryl ketones have been proved valuable starting materials in organic synthesis[4]. Thus, we synthesised (2-hydroxyphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone oxime and we subsequently oxidized it with diacetoxy iodobenzene (DIB). The reaction led to the formation of the oxidative cyclisation product, giving the desired 3-(1-phenyl-1H-pyrazol-4-yl)-1,2-benzisoxazole 2-oxide, in 61% yield. (2-Hydroxyphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone oxime was prepared according to the literature methods by refluxing (2-hydroxyphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone and hydrochloric hydroxylamine in ethanol in the presence of pyridine whereas commercially available diacetoxy iodobenzene were supplied by Aldrich. Oxidation of (2-hydroxyphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone oxime0.58 g (1.79 mmol) of DIB are added to a suspension of 0.5 g (1.79 mmol) of (2-hydroxyphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone oxime in 20 ml CH2Cl2 in an ice-bath. The mixture was then magnetically stirred for 3 hrs. Evaporation of the solvent gave an oil which was then subjected to column chromatography (silica gel 70-230 mesh). Elution with a mixture of petroleum ether / ethylacetate 3:1 afforded the desired 3-(1-phenyl-1H-pyrazol-4-yl)-1,2-benzisoxazole 2-oxide as white crystals (0.30 g, 61 %). The product was identified by its 1H NMR, 13C NMR and MS and elemental analysis. M.p. 179-180 °C.1H NMR (400 MHz, DMSO-d6): 7.44-7.52 (m, 3H), 7.58-7.70 (m, 3H), 8.04-8.07(m, 2H), 8.32-8.34(d, J=8.0Hz, 1H), 8.67(s, 1H), 9.36(s, 1H).13C NMR (100 MHz, DMSO-d6): 107.7, 109.5, 118.9, 119.9, 120.1, 121.6, 125.1, 127.3, 127.7, 128.1, 129.6, 130.2, 139.5, 139.7, 149.1, 150.5.MS m/z (ES+): 300 [M+Na]+, 277 [M]+, 261, 247.Anal. Calc. for C16H11N3O2: C 69.31, H 4.00, N 15.15; found: C 69.22, H 3.88, N, 15.10 Supplementary materialsSupplementary File 1Supplementary File 2Supplementary File 3ReferencesPriya, B.S.; Bassappa, S.; Nanjunda, S.; Rangappa, S. Biorganic and Med. Chem. 2005, 13, 2623. [CrossRef]Menozzi, G.; Merello, L.; Fossa, P.; Schenome, S.; Ranise, A.; Mosti, L.; Bondavalli, F.; Loddo, R.; Murgioni, C.; Mascia, V.; La Colla, P.; Tamburini, E. Bioorg. Med. Chem. 2004, 12(20), 5465. [CrossRef] [PubMed]Bekhit, A.A.; Ashour, H.M.; Guemei, A.A. Arch Pharm (Weinheim) 2005, 338(4), 167. [PubMed]Kotali, A.; Harris, P.A. Org. Prep. Proc. Int. 1994, 26(2), 155. © 2008 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). Share and Cite MDPI and ACS Style Kotali, A. 3-(1-Phenyl-1H-pyrazol-4-yl)-1,2-benzisoxazole 2-oxide. Molbank 2008, 2008, M573. https://doi.org/10.3390/M573 AMA Style Kotali A. 3-(1-Phenyl-1H-pyrazol-4-yl)-1,2-benzisoxazole 2-oxide. Molbank. 2008; 2008(2):M573. https://doi.org/10.3390/M573 Chicago/Turabian Style Kotali, Antigoni. 2008. 3-(1-Phenyl-1H-pyrazol-4-yl)-1,2-benzisoxazole 2-oxide Molbank 2008, no. 2: M573. https://doi.org/10.3390/M573 Find Other Styles Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here. Article Metrics No No Article Access Statistics For more information on the journal statistics, click here. Multiple requests from the same IP address are counted as one view." @default.
• W2075737008 created "2016-06-24" @default.
• W2075737008 creator A5064569138 @default.
• W2075737008 date "2008-08-24" @default.
• W2075737008 modified "2023-09-26" @default.
• W2075737008 title "3-(1-Phenyl-1H-pyrazol-4-yl)-1,2-benzisoxazole 2-oxide" @default.
• W2075737008 cites W1969036487 @default.
• W2075737008 cites W2022736601 @default.
• W2075737008 cites W2086974181 @default.
• W2075737008 cites W2149878615 @default.
• W2075737008 doi "https://doi.org/10.3390/m573" @default.
• W2075737008 hasPublicationYear "2008" @default.
• W2075737008 type Work @default.
• W2075737008 sameAs 2075737008 @default.
• W2075737008 citedByCount "2" @default.
• W2075737008 countsByYear W20757370082012 @default.
• W2075737008 crossrefType "journal-article" @default.
• W2075737008 hasAuthorship W2075737008A5064569138 @default.
• W2075737008 hasBestOaLocation W20757370081 @default.
• W2075737008 hasConcept C134121241 @default.
• W2075737008 hasConcept C155647269 @default.
• W2075737008 hasConcept C161790260 @default.
• W2075737008 hasConcept C178790620 @default.
• W2075737008 hasConcept C185592680 @default.
• W2075737008 hasConcept C191897082 @default.
• W2075737008 hasConcept C192562407 @default.
• W2075737008 hasConcept C2776451764 @default.
• W2075737008 hasConcept C2777682936 @default.
• W2075737008 hasConcept C2779648554 @default.
• W2075737008 hasConcept C2780378348 @default.
• W2075737008 hasConcept C2781269603 @default.
• W2075737008 hasConceptScore W2075737008C134121241 @default.
• W2075737008 hasConceptScore W2075737008C155647269 @default.
• W2075737008 hasConceptScore W2075737008C161790260 @default.
• W2075737008 hasConceptScore W2075737008C178790620 @default.
• W2075737008 hasConceptScore W2075737008C185592680 @default.
• W2075737008 hasConceptScore W2075737008C191897082 @default.
• W2075737008 hasConceptScore W2075737008C192562407 @default.
• W2075737008 hasConceptScore W2075737008C2776451764 @default.
• W2075737008 hasConceptScore W2075737008C2777682936 @default.
• W2075737008 hasConceptScore W2075737008C2779648554 @default.
• W2075737008 hasConceptScore W2075737008C2780378348 @default.
• W2075737008 hasConceptScore W2075737008C2781269603 @default.
• W2075737008 hasIssue "2" @default.
• W2075737008 hasLocation W20757370081 @default.
• W2075737008 hasOpenAccess W2075737008 @default.
• W2075737008 hasPrimaryLocation W20757370081 @default.
• W2075737008 hasRelatedWork W1492047339 @default.
• W2075737008 hasRelatedWork W1969486137 @default.
• W2075737008 hasRelatedWork W1986683225 @default.
• W2075737008 hasRelatedWork W2011746025 @default.
• W2075737008 hasRelatedWork W2075737008 @default.
• W2075737008 hasRelatedWork W2097014657 @default.
• W2075737008 hasRelatedWork W2168356616 @default.
• W2075737008 hasRelatedWork W2223706456 @default.
• W2075737008 hasRelatedWork W2549569279 @default.
• W2075737008 hasRelatedWork W2769513459 @default.
• W2075737008 hasVolume "2008" @default.
• W2075737008 isParatext "false" @default.
• W2075737008 isRetracted "false" @default.
• W2075737008 magId "2075737008" @default.
• W2075737008 workType "article" @default.