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Unanticipated stereoselectivity in the reaction of primaquine α-aminoamides with substituted benzaldehydes:  A computational and experimental study†

2007-05-03Journal article Restricted access
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dc.contributor.authorFerraz, Ricardo
dc.contributor.authorGomes, José R. B.
dc.contributor.authorOliveira, Eliandre de
dc.contributor.authorMoreira, Rui
dc.contributor.authorGomes, Paula
dc.date.accessioned2021-10-20T10:52:21Z
dc.date.available2021-10-20T10:52:21Z
dc.date.issued2007-05-03
dc.description.abstractImidazolidin-4-ones are commonly employed as skeletal modifications in bioactive oligopeptides, either as proline surrogates or for protection of the N-terminal amino acid against aminopeptidase- and endopeptidase-catalyzed hydrolysis. Imidazolidin-4-one synthesis usually involves the reaction of an α-aminoamide moiety with a ketone or an aldehyde to yield an imine, followed by intramolecular cyclization. We have unexpectedly found that imidazolidin-4-one formation is stereoselective when benzaldehydes containing o-carboxyl or o-methoxycarbonyl substituents are reacted with α-aminoamide derivatives of the antimalarial drug primaquine. A systematic computational and experimental study on the stereoselectivity of imidazolidin-4-one formation from primaquine α-aminoamides and various substituted benzaldehydes has been carried out, and they have allowed us to conclude that intramolecular hydrogen-bonds involving the CO oxygen of the o-substituent play a crucial role.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationFerraz, R., Gomes, J. R. B., de Oliveira, E., Moreira, R., & Gomes, P. (2007). Unanticipated Stereoselectivity in the Reaction of Primaquine α-Aminoamides with Substituted Benzaldehydes:  A Computational and Experimental Study. The Journal of Organic Chemistry, 72(11), 4189-4197. https://doi.org/10.1021/jo0703202pt_PT
dc.identifier.doi10.1021/jo0703202pt_PT
dc.identifier.eissn1520-6904
dc.identifier.urihttp://hdl.handle.net/10400.22/18746
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherACS Publicationspt_PT
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/jo0703202pt_PT
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/pt_PT
dc.subjectImidazolidin-4-onespt_PT
dc.subjectN-terminal aminoacidpt_PT
dc.subjectα-aminoamide moietypt_PT
dc.titleUnanticipated stereoselectivity in the reaction of primaquine α-aminoamides with substituted benzaldehydes:  A computational and experimental study†pt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage4197pt_PT
oaire.citation.startPage4189pt_PT
oaire.citation.titleThe Journal of Organic Chemistrypt_PT
oaire.citation.volume72pt_PT
person.familyNameFerraz
person.givenNameRicardo
person.identifier.ciencia-id001E-71CE-F92D
person.identifier.orcid0000-0002-1761-117X
person.identifier.ridG-5639-2011
person.identifier.scopus-author-id24464208500
rcaap.rightsclosedAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublicationa5a8faa7-12a5-4b1c-bced-44c895677397
relation.isAuthorOfPublication.latestForDiscoverya5a8faa7-12a5-4b1c-bced-44c895677397

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