Regioselective Synthesis of C3-Hydroxyarylated Pyrazoles

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dc.contributor.authorLeonie O’Sullivan
dc.contributor.authorKetul V. Patel
dc.contributor.authorBen C. Rowley
dc.contributor.authorDuncan K. Brownsey
dc.contributor.authorEvgueni Gorobets
dc.contributor.authorBenjamin S. Gelfand
dc.contributor.authorJeffrey F. Van Humbeck
dc.contributor.authorDarren J. Derksen
dc.date.accessioned2024-04-10T21:11:52Z
dc.date.available2024-04-10T21:11:52Z
dc.date.issued2021-12-14
dc.description.abstractPyrazoles are ubiquitous structures in medicinal chemistry. We report the first regioselective route to C3-hydroxyarylated pyrazoles obtained through reaction of pyrazole N-oxides with arynes using mild conditions. Importantly, this method does not require the C4 and C5 positions of the pyrazole to be functionalized to observe regioselectivity. Using this method, we completed the synthesis of a recently reported JAK 1/2 inhibitor. Our synthesis produces the desired product in 4 steps from commercially available starting materials.
dc.description.grantingagencyNatural Sciences and Engineering Research Council (NSERC)
dc.identifier.citationO’Sullivan, L., Patel, K. V., Rowley, B. C., Brownsey, D. K., Gorobets, E., Gelfand, B. S., Van Humbeck, J. F., & Derksen, D. J. (2022). Regioselective Synthesis of C3-Hydroxyarylated Pyrazoles. The Journal of Organic Chemistry, 87(1), 846–854. https://doi.org/10.1021/acs.joc.1c02518
dc.identifier.doihttps://doi.org/10.1021/acs.joc.1c02518
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttps://hdl.handle.net/1880/118361
dc.identifier.urihttps://doi.org/10.11575/PRISM/43203
dc.language.isoenen
dc.publisherAmerican Chemical Society
dc.publisher.facultyScienceen
dc.publisher.hasversionacceptedVersion
dc.publisher.institutionUniversity of Calgaryen
dc.publisher.policyhttps://pubs.acs.org/page/copyright/index.html
dc.relation.ispartofThe Journal of Organic Chemistry
dc.rightsUnless otherwise indicated, this material is protected by copyright and has been made available with authorization from the copyright owner. You may use this material in any way that is permitted by the Copyright Act or through licensing that has been assigned to the document. For uses that are not allowable under copyright legislation or licensing, you are required to seek permission.en
dc.subjectChromatography
dc.subjectEthyl groups
dc.subjectgels
dc.subjectorganic compounds
dc.subjectsilica
dc.titleRegioselective Synthesis of C3-Hydroxyarylated Pyrazoles
dc.typeArticle
oaire.citation.issue1
oaire.citation.volume87
ucalgary.scholar.levelFaculty
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