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Synthesis of novel pyrazolo[3,4-b]quinoline-bisphosphonic acids and an unexpected intramolecular cyclization and phosphonylation reaction

2021-03Journal article Embargoed access
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dc.contributor.authorTeixeira, Fatima
dc.contributor.authorLucas, Carla
dc.contributor.authorCurto, Maria João Marcelo
dc.contributor.authorAndre, Vania
dc.contributor.authorDuarte, M. Teresa
dc.contributor.authorTeixeira, António P. S.
dc.date.accessioned2022-01-06T16:54:02Z
dc.date.embargo2026-12
dc.date.issued2021-03
dc.description.abstractABSTRACT: Novel pyrazolo[3,4-b]quinoline alpha-ketophosphonic and hydroxymethylenebisphosphonic acid compounds were synthesized using different methodologies, starting from 2-chloro-3-formylquinoline 1. New phosphonic acid compounds were obtained as N-1 derivatives with a side chain with 1 or 3 (n = 1 or 3) methylene groups. All phosphonic acid compounds and their corresponding ester and carboxylic acid precursors were fully characterized, and their structures elucidated by spectroscopic data, using NMR techniques and infrared and high-resolution mass spectroscopy. During the process to obtain the N-1 substituted derivative with two methylene groups (n = 2) in the side chain, an unexpected addition-cyclization cascade reaction was observed, involving the phosphonylation of an aromatic ring and the formation of a new six-member lactam ring to afford a tetracyclic ring system. This was an unexpected result since other pyrazolo[3,4-b]quinoline derivatives and all corresponding pyrazolo[3,4-b]pyridine derivatives already prepared, under similar experimental conditions, did not undergo this reaction. This domino reaction occurs with different phosphite reagents but only affords the six-member ring. The spectroscopic data allowed the identification of the new synthesized tetracyclic compounds and the X-ray diffraction data of compound 11 enabled the confirmation of the proposed structures.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationTeixeira, Fátima C... [et.al.] - Synthesis of novel pyrazolo[3,4-b]quinoline-bisphosphonic acids and an unexpected intramolecular cyclization and phosphonylation reaction. In: Organic and Biomolecular Chemistry, 2021, Vol. 19 (11), p. 2533-2545pt_PT
dc.identifier.doi10.1039/d1ob00025jpt_PT
dc.identifier.eissn1477-0539
dc.identifier.issn1477-0520
dc.identifier.urihttp://hdl.handle.net/10400.9/3678
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherRoyal Society of Chemistrypt_PT
dc.relationPest-OE/QUI/UI0619/2019pt_PT
dc.relationCentro de Química Estrutural
dc.relation.publisherversionhttps://doi.org/10.1039/d1ob00025jpt_PT
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectBisphosphonatespt_PT
dc.subjectX-ray diffractionpt_PT
dc.subjectIndazolept_PT
dc.subjectPyrazolo[3,4-b]pyridinept_PT
dc.subjectPyrazolo[3,4-b]quinolinept_PT
dc.titleSynthesis of novel pyrazolo[3,4-b]quinoline-bisphosphonic acids and an unexpected intramolecular cyclization and phosphonylation reactionpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCentro de Química Estrutural
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/POCI/POCI%2FQUI%2F55508%2F2004/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PPCDT%2FQUI%2F55508%2F2004/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F00100%2F2020/PT
oaire.citation.endPage2545pt_PT
oaire.citation.issue11pt_PT
oaire.citation.startPage2533pt_PT
oaire.citation.titleOrganic and Biomolecular Chemistrypt_PT
oaire.citation.volume19pt_PT
oaire.fundingStreamPOCI
oaire.fundingStream3599-PPCDT
oaire.fundingStream6817 - DCRRNI ID
person.familyNameTeixeira
person.familyNameAndre
person.familyNameDuarte
person.familyNameTeixeira
person.givenNameFatima
person.givenNameVania
person.givenNameMaria Teresa
person.givenNameAntónio Paulo Silva
person.identifier1017457
person.identifier.ciencia-idC014-509B-D1DC
person.identifier.ciencia-id5D11-03DB-AB4F
person.identifier.ciencia-id7E16-5ED4-ED6A
person.identifier.orcid0000-0003-0801-2068
person.identifier.orcid0000-0001-5599-8355
person.identifier.orcid0000-0003-0994-1352
person.identifier.orcid0000-0001-7448-0893
person.identifier.ridA-3006-2011
person.identifier.ridH-8658-2012
person.identifier.ridN-5456-2014
person.identifier.scopus-author-id7102746385
person.identifier.scopus-author-id22233327400
person.identifier.scopus-author-id6505770075
person.identifier.scopus-author-id36856362300
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsembargoedAccesspt_PT
rcaap.typearticlept_PT
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