(E)-2-(4-Arylbut-1-en-3-yn-1-yl)chromones as synthons for the synthesis of xanthone-1,2,3-triazole dyads

Albuquerque, Hélio; Santos, Clementina M.M.; Cavaleiro, José; Silva, Artur

Publication

(E)-2-(4-Arylbut-1-en-3-yn-1-yl)chromones as synthons for the synthesis of xanthone-1,2,3-triazole dyads

2015Journal article

dc.contributor.author	Albuquerque, Hélio
dc.contributor.author	Santos, Clementina M.M.
dc.contributor.author	Cavaleiro, José
dc.contributor.author	Silva, Artur
dc.date.accessioned	2016-01-07T14:21:51Z
dc.date.available	2016-01-07T14:21:51Z
dc.date.issued	2015
dc.description.abstract	Xanthone-1,2,3-triazole dyads have been synthesized by two different approaches, both starting from novel (E)-2-(4-arylbut-1-en-3-yn-1-yl)chromones, prepared through a base-catalyzed aldol reaction of 2-methylchromone and arylpropargyl aldehydes. In the first method, the xanthone moiety is built by Diels-Alder reaction of the referred unsaturated chromones with N-methylmaleimide under microwave irradiation, followed by oxidation of the obtained adducts with DDQ, whereas the 1,2,3-triazole ring results from the cycloaddition reaction of the acetylene moiety with sodium azide. The second strategy first involves the cycloaddition reaction with sodium azide to provide the 1,2,3-triazole ring, followed by methylation of the triazole NH group prior to Diels-Alder reaction with N-methylmaleimide. The last step in this synthesis of novel xanthone-1,2,3-triazole dyads entails oxidation of the cycloadducts with DDQ.	pt_PT
dc.identifier.citation	Albuquerque, Hélio; Santos, Clementina M.M.; Cavaleiro, José; Silva, Artur (2015). (E)-2-(4-Arylbut-1-en-3-yn-1-yl)chromones as synthons for the synthesis of xanthone-1,2,3-triazole dyads. European Journal of Organic Chemistry. ISSN 1434-193X. 21, p. 4732-4743	pt_PT
dc.identifier.doi	10.1002/ejoc.201500448	pt_PT
dc.identifier.issn	1434-193X
dc.identifier.uri	http://hdl.handle.net/10198/12559
dc.language.iso	eng	pt_PT
dc.peerreviewed	yes	pt_PT
dc.relation	NOVAS ROTAS DE SÍNTESE DE FLAVONAS E XANTONAS: REAÇÕES DE CICLOADIÇÃO E DE ACOPLAMENTO CRUZADO CATALISADAS POR PALÁDIO
dc.rights.uri	http://creativecommons.org/licenses/by/4.0/	pt_PT
dc.subject	Cycloaddition	pt_PT
dc.subject	Diels-Alder reaction	pt_PT
dc.subject	Cyclization	pt_PT
dc.subject	Click chemistry	pt_PT
dc.subject	Oxygen heterocycles	pt_PT
dc.subject	Nitrogen heterocycles	pt_PT
dc.title	(E)-2-(4-Arylbut-1-en-3-yn-1-yl)chromones as synthons for the synthesis of xanthone-1,2,3-triazole dyads	pt_PT
dc.type	journal article
dspace.entity.type	Publication
oaire.awardTitle	NOVAS ROTAS DE SÍNTESE DE FLAVONAS E XANTONAS: REAÇÕES DE CICLOADIÇÃO E DE ACOPLAMENTO CRUZADO CATALISADAS POR PALÁDIO
oaire.awardURI	info:eu-repo/grantAgreement/FCT/COMPETE/PEst-C%2FQUI%2FUI0062%2F2013/PT
oaire.awardURI	info:eu-repo/grantAgreement/FCT/FARH/SFRH%2FBD%2F86277%2F2012/PT
oaire.citation.title	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY	pt_PT
oaire.fundingStream	COMPETE
oaire.fundingStream	FARH
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	article	pt_PT
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