Utilize este identificador para referenciar este registo: http://hdl.handle.net/10451/21517
Título: Unanticipated stereoselectivity in the reaction of primaquine alpha-aminoamides with substituted benzaldehydes
A computational and experimental study
Autor: Ferraz, Ricardo
Gomes, Jose R. B.
de Oliveira, Eliandre
Moreira, Rui
Gomes, Paula
Palavras-chave: Chemistry, Organic
Data: 2007
Citação: JOURNAL OF ORGANIC CHEMISTRY. - Vol. 72, n. 11 (MAY 25 2007), p. 4189-4197
Resumo: Imidazolidin-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 alpha-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 alpha-aminoamide derivatives of the antimalarial drug primaquine. A systematic computational and experimental study on the stereoselectivity of imidazolidin-4-one formation from primaquine alpha-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.
URI: http://hdl.handle.net/10451/21517
DOI: http://dx.doi.org/10.1021/jo0703202
ISSN: 0022-3263
Aparece nas colecções:FF - Produção Científica 2000-2009

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