Utilize este identificador para referenciar este registo: http://hdl.handle.net/10400.22/2007
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dc.contributor.authorFerraz, Ricardo-
dc.contributor.authorGomes, José R. B.-
dc.contributor.authorPasso, Joana-
dc.contributor.authorOliveira, Eliandre-
dc.contributor.authorMoreira, Rui-
dc.contributor.authorGomes, Paula-
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-catalysed hydrolysis . We have been working on the synthesis of imidazolidin-4-ones of the antimalarial primaquine , through acylation of primaquine with an α-amino acid and subsequent reaction of the resulting α-aminoamide with a ketone or aldehyde. Thus, when using racemic primaquine, an optically pure chiral α-amino acid and an aldehyde as starting materials, four imidazolidin-4-one diastereomers are to be expected (Scheme 1). However, we have recently observed that imidazolidin-4-one synthesis was stereoselective when 2-carboxybenzaldehyde (2CBA)* was used, as only two diastereomers were produced2. Computational studies have shown that the imine formed prior to ring closure had, for structures derived from 2CBA, a quasi-cyclic rigid structure2. This rigid conformation is stabilized by an intramolecular hydrogen bond involving the C=O oxygen atom of the 2-carboxyl substituent in 2CBA and the N-H group of the α-amino amide moiety2. These findings led us to postulate that the 2-carbonyl substituent in the benzaldehyde moiety was the key for the stereoselective synthesis of the imidazolidin-4-ones2.por
dc.publisherInstituto Politécnico do Porto. Escola Superior de Tecnologia da Saúde do Portopor
dc.publisherUniversidade do Porto. Faculdade de Ciências da Universidade do Porto-
dc.publisherUniversidade do Porto. Faculdade de Farmácia da Universidade do Porto-
dc.publisherBarcelona Science Park-
dc.titleSteroselective synthesis of imidazolidin-4-ones from α-amino amides of the antimalarial primaquine and substituted benzaldehydespor
degois.publication.locationSantiago de Compostela, Espanhapor
degois.publication.title4th Spanish-Portuguese-Japanese Organic Chemistry Symposiumpor
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