Publication
Synthesis of xanthone-1,2,3-triazole dyads
| dc.contributor.author | Albuquerque, Hélio | |
| dc.contributor.author | Santos, Clementina M.M. | |
| dc.contributor.author | Silva, Artur | |
| dc.contributor.author | Cavaleiro, José | |
| dc.date.accessioned | 2016-05-30T10:54:01Z | |
| dc.date.available | 2016-05-30T10:54:01Z | |
| dc.date.issued | 2015 | |
| dc.description.abstract | Xanthones and 1,2,3-triazoles are known to exhibit several biological, pharmacological and biocidal properties[1]. The potential applications of these two classes of heterocycles led us to develop new strategies to synthesize xanthone-1,2,3-triazole dyads, aiming to get potentially improved therapeutic agents[2]. With this rational in mind we designed and synthesized novel chromone derivatives 1a-d to be used as building motifs and to explore the reactivity of the two unsaturated systems (the diene and the alkyne). In the present communication we will present a new synthetic route towards the synthesis of xanthone-1,2,3-triazole dyads 7a-d using consecutively the azide-alkyne Huisgen 1,3-dipolar cycloaddition and Diels-Alder reaction. Our approach involves the synthesis chromone-triazole derivatives 2a-d using the reaction of 1a-d with sodium azide, followed by the methylation of the NH of the triazole moiety. The methylation afforded three isomers 3a-d, 4a-d and 5a-d, as expected. The major isomers 3a-d were used in the Diels-Alder reaction with N-methylmaleimide, and the adducts obtained 6a-d were oxidized to afford the xanthone-1,2,3-triazole dyads 7a-d. All the synthetic details as well as the structural characterization (by 1D and 2D NMR studies) of the new synthesised compounds will be presented and discussed. | pt_PT |
| dc.identifier.citation | Albuquerque, Hélio; Santos, Clementina M.M.; Silva, Artur; Cavaleiro, José (2015). Synthesis of xanthone-1,2,3-triazole dyads. In 19th European Symposium on Organic Chemistry. Lisboa | pt_PT |
| dc.identifier.uri | http://hdl.handle.net/10198/12944 | |
| dc.language.iso | eng | pt_PT |
| dc.peerreviewed | yes | pt_PT |
| dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | pt_PT |
| dc.title | Synthesis of xanthone-1,2,3-triazole dyads | pt_PT |
| dc.type | conference object | |
| dspace.entity.type | Publication | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT/5876/UID%2FQUI%2F00062%2F2013/PT | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBD%2F86277%2F2012/PT | |
| oaire.citation.conferencePlace | Lisboa | pt_PT |
| oaire.citation.title | 19th European Symposium on Organic Chemistry | pt_PT |
| oaire.fundingStream | 5876 | |
| oaire.fundingStream | SFRH | |
| person.familyName | Santos | |
| person.givenName | Clementina M.M. | |
| person.identifier.ciencia-id | 9018-DB9C-C590 | |
| person.identifier.orcid | 0000-0003-4380-7990 | |
| person.identifier.scopus-author-id | 7201458663 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| rcaap.rights | openAccess | pt_PT |
| rcaap.type | conferenceObject | pt_PT |
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