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https://hdl.handle.net/1822/72914
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Campo DC | Valor | Idioma |
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dc.contributor.author | Ferreira, Paula M. T. | por |
dc.contributor.author | Monteiro, Luís S. | por |
dc.contributor.author | Pereira, Goreti | por |
dc.date.accessioned | 2021-05-27T14:16:28Z | - |
dc.date.available | 2021-05-27T14:16:28Z | - |
dc.date.issued | 2008-09 | - |
dc.identifier.issn | 1434-193X | por |
dc.identifier.uri | https://hdl.handle.net/1822/72914 | - |
dc.description.abstract | Several N-acyl-beta-hydroxyamino acids were prepared and treated with di-tert-butyl dicarbonate in the presence of 4-(dimethylamino)pyridine, followed by treatment with N,N,N',N'-tetramethylguanidine to give the corresponding N-acyldehydroamino acids in good to high yields. These were then treated with I-2/K2CO3 followed by 1,8-diazabicyclo[5.4.0]undec-7-ene. The methyl esters of N-acyldehydroaminobutyric acid gave the corresponding substituted oxazoles in good to high yields. The N-acyldehydrophenylalanines gave 5-phenyloxazole derivatives in low to moderate yields together with beta-iododehydrophenylalanines. Under the same conditions, N-acyldehydroalanines failed to give the corresponding oxazoles. However, when the reaction was carried out in the absence of DBU, it was possible to isolate the beta,beta-diiododehydroalanine derivatives. Although the reason for the different reactivities of the N-acyldehydroamino acids is not completely clear to us, cyclic voltammetry studies showed that the less-reactive derivatives have higher reduction potentials. This suggests that the double bonds in dehydroaminobutyric acid derivatives are more susceptible to electrophilic attack by iodine. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008). | por |
dc.description.sponsorship | - The Foundation for Science and Technology (FCT) - Portugal and FEDER for financial support through the Centro de Quimica of the Univ. of Minho and through project POCI/QUI/59407/2004. | por |
dc.language.iso | eng | por |
dc.publisher | Wiley-VCH Verlag | por |
dc.relation | info:eu-repo/grantAgreement/FCT/POCI/59407/PT | por |
dc.rights | openAccess | por |
dc.subject | Amino acids | por |
dc.subject | Dehydroamino acids | por |
dc.subject | Iodine | por |
dc.subject | Cyclization | por |
dc.subject | Oxygen heterocycles | por |
dc.subject | Nitrogen heterocyles | por |
dc.title | Synthesis of substituted oxazoles from N-acyl-beta-hydroxyamino acid derivatives | por |
dc.type | article | - |
dc.peerreviewed | yes | por |
dc.relation.publisherversion | https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.200800602 | por |
oaire.citationStartPage | 4676 | por |
oaire.citationEndPage | 4683 | por |
oaire.citationIssue | 27 | por |
dc.date.updated | 2021-05-24T15:09:28Z | - |
dc.identifier.doi | 10.1002/ejoc.200800602 | por |
dc.subject.wos | Science & Technology | - |
sdum.export.identifier | 10821 | - |
sdum.journal | European Journal of Organic Chemistry | por |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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2008-Eur. J. Org. Chem. 4676.pdf | 208,17 kB | Adobe PDF | Ver/Abrir |