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

Title
Unanticipated stereoselectivity in the reaction of primaquine alpha-aminoamides with substituted benzaldehydes: A computational and experimental study
Type
Article in International Scientific Journal
Year
2007
Authors
Ricardo Ferraz
(Author)
Other
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Eliandre de Oliveira
(Author)
Other
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Rui Moreira
(Author)
Other
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Journal
Vol. 72
Pages: 4189-4197
ISSN: 0022-3263
Scientific classification
FOS: Natural sciences > Chemical sciences
Other information
Authenticus ID: P-004-A28
Abstract (EN): 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.
Language: English
Type (Professor's evaluation): Scientific
License type: Click to view license CC BY-NC
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