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Acid and base catalyzed Davis-Beirut reaction: Experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles

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dc.contributor.author Avila B.
dc.contributor.author El-Dakdouki M.H.
dc.contributor.author Nazer M.Z.
dc.contributor.author Harrison J.G.
dc.contributor.author Tantillo D.J.
dc.contributor.author Haddadin M.J.
dc.contributor.author Kurth M.J.
dc.contributor.editor
dc.date 2012
dc.date.accessioned 2017-10-03T15:45:30Z
dc.date.available 2017-10-03T15:45:30Z
dc.date.issued 2012
dc.identifier 10.1016/j.tetlet.2012.09.026
dc.identifier.isbn
dc.identifier.issn 00404039
dc.identifier.uri http://hdl.handle.net/10938/12680
dc.description.abstract The Davis-Beirut reaction, which provides an efficient synthesis of 2H-indazoles and, subsequently, indazolones, is shown to proceed rapidly from o-nitrosobenzaldehyde and primary amines under both acid and base catalysis. Experimental and theoretical evidence in support of a reaction mechanism is provided in which o-nitrosobenzylidine imine is a pivotal intermediate in this N,N-bond forming heterocyclization reaction. The Davis-Beirut reaction is also shown to effectively synthesize a number of novel 3-amino-2H-indazole derivatives. © 2012 Elsevier Ltd. All rights reserved.
dc.format.extent
dc.format.extent Pages: (6475-6478)
dc.language English
dc.publisher OXFORD
dc.relation.ispartof Publication Name: Tetrahedron Letters; Publication Year: 2012; Volume: 53; no. 48; Pages: (6475-6478);
dc.relation.ispartofseries
dc.relation.uri
dc.source Scopus
dc.subject.other
dc.title Acid and base catalyzed Davis-Beirut reaction: Experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles
dc.type Article
dc.contributor.affiliation Avila, B., Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, United States
dc.contributor.affiliation El-Dakdouki, M.H., Department of Chemistry, American University of Beirut, Bliss Street, Lebanon
dc.contributor.affiliation Nazer, M.Z., Department of Chemistry, University of Jordan, Queen Alia Boulevard, Amman, Jordan
dc.contributor.affiliation Harrison, J.G., Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, United States
dc.contributor.affiliation Tantillo, D.J., Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, United States
dc.contributor.affiliation Haddadin, M.J., Department of Chemistry, American University of Beirut, Bliss Street, Lebanon
dc.contributor.affiliation Kurth, M.J., Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, United States
dc.contributor.authorAddress Kurth, M.J.; Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, United States; email: mjkurth@ucdavis.edu
dc.contributor.authorCorporate University: American University of Beirut; Faculty: Faculty of Arts and Sciences; Department: Chemistry;
dc.contributor.authorDepartment Chemistry
dc.contributor.authorDivision
dc.contributor.authorEmail mjkurth@ucdavis.edu
dc.contributor.faculty Faculty of Arts and Sciences
dc.contributor.authorInitials Avila, B
dc.contributor.authorInitials El-Dakdouki, MH
dc.contributor.authorInitials Nazer, MZ
dc.contributor.authorInitials Harrison, JG
dc.contributor.authorInitials Tantillo, DJ
dc.contributor.authorInitials Haddadin, MJ
dc.contributor.authorInitials Kurth, MJ
dc.contributor.authorOrcidID
dc.contributor.authorReprintAddress Kurth, MJ (reprint author), Univ Calif Davis, Dept Chem, 1 Shields Ave, Davis, CA 95616 USA.
dc.contributor.authorResearcherID
dc.contributor.authorUniversity American University of Beirut
dc.description.cited Avila B, 2011, ORG LETT, V13, P1060, DOI 10.1021-ol103108z; Bamberger E., 1918, CHEM BER, V51, P606; Butler JD, 2008, J ORG CHEM, V73, P234, DOI 10.1021-jo702067z; Cankarova N, 2010, ORG PREP PROCED INT, V42, P433, DOI 10.1080-00304948.2010.513898; Chen LJ, 1998, TETRAHEDRON LETT, V39, P5351, DOI 10.1016-S0040-4039(98)01068-5; Conrad W. E., 2011, ORG LETT, V13, P2141; Conrad WE, 2012, ORG LETT, V14, P3870, DOI 10.1021-ol3015804; De Angelis M, 2005, J MED CHEM, V48, P1132, DOI 10.1021-jm049223g; DEWAR MJS, 1984, J AM CHEM SOC, V106, P209, DOI 10.1021-ja00313a042; Donald MB, 2010, ORG LETT, V12, P2524, DOI 10.1021-ol100751n; Haddadin MJ, 2012, MINI-REV MED CHEM, V12, P1293; Huang LJ, 2006, BIOORGAN MED CHEM, V14, P528, DOI 10.1016-j.bmc.2005.08.032; Jung N., 2010, SCI SYNTH, V41, P613; Kurth MJ, 2005, J ORG CHEM, V70, P1060, DOI 10.1021-jo048153i; Mills AD, 2007, J COMB CHEM, V9, P171, DOI 10.1021-cc060109o; Mills AD, 2006, J ORG CHEM, V71, P2687, DOI 10.1021-jo0524831; Oakdale JS, 2009, ORG LETT, V11, P2760, DOI 10.1021-ol900891s; Schmidt A, 2008, EUR J ORG CHEM, P4073, DOI 10.1002-ejoc.200800227; Solano D. M., 2010, ORG SYNTH, V87, P339; Stadlbauer W., 2002, SCI SYNTH, V12, P227; Tantillo DJ, 2008, J PHYS ORG CHEM, V21, P561, DOI 10.1002-poc.1320; Williams A., 2000, CONCERTED ORGANIC BI; Wu CR, 2010, ORG LETT, V12, P2234, DOI 10.1021-ol100586r
dc.description.citedCount 2
dc.description.citedTotWOSCount 3
dc.description.citedWOSCount 3
dc.format.extentCount 4
dc.identifier.articleNo
dc.identifier.coden TELEA
dc.identifier.pubmedID
dc.identifier.scopusID 84867899590
dc.identifier.url
dc.publisher.address THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
dc.relation.ispartofConference
dc.relation.ispartofConferenceCode
dc.relation.ispartofConferenceDate
dc.relation.ispartofConferenceHosting
dc.relation.ispartofConferenceLoc
dc.relation.ispartofConferenceSponsor
dc.relation.ispartofConferenceTitle
dc.relation.ispartofFundingAgency
dc.relation.ispartOfISOAbbr Tetrahedron Lett.
dc.relation.ispartOfIssue 48
dc.relation.ispartOfPart
dc.relation.ispartofPubTitle Tetrahedron Letters
dc.relation.ispartofPubTitleAbbr Tetrahedron Lett.
dc.relation.ispartOfSpecialIssue
dc.relation.ispartOfSuppl
dc.relation.ispartOfVolume 53
dc.source.ID WOS:000311021600001
dc.type.publication Journal
dc.subject.otherAuthKeyword 2H-Indazole
dc.subject.otherAuthKeyword Catalysis
dc.subject.otherAuthKeyword Davis-Beirut reaction
dc.subject.otherAuthKeyword Mechanism
dc.subject.otherAuthKeyword o-Nitrosobenzaldehyde
dc.subject.otherChemCAS imine, 13774-92-0
dc.subject.otherIndex 3 amino 2h indazole derivative
dc.subject.otherIndex amine
dc.subject.otherIndex benzaldehyde derivative
dc.subject.otherIndex imine
dc.subject.otherIndex indazole derivative
dc.subject.otherIndex unclassified drug
dc.subject.otherIndex article
dc.subject.otherIndex catalysis
dc.subject.otherIndex chemical bond
dc.subject.otherIndex chemical reaction
dc.subject.otherIndex davis beirut reaction
dc.subject.otherIndex experimental study
dc.subject.otherIndex reaction analysis
dc.subject.otherIndex theoretical study
dc.subject.otherKeywordPlus ROUTE
dc.subject.otherKeywordPlus 1H-INDAZOLONES
dc.subject.otherKeywordPlus INDAZOLES
dc.subject.otherWOS Chemistry, Organic


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