Utilize este identificador para referenciar este registo: http://hdl.handle.net/10451/21673
Título: Amino acids as selective acylating agents
regioselective N-1-acylation of imidazolidin-4-one derivatives of the antimalarial drug primaquine
Autor: Vale, Nuno
Matos, Joana
Moreira, Rui
Gomes, Paula
Palavras-chave: Chemistry, Organic
Data: 2008
Editora: PERGAMON-ELSEVIER SCIENCE LTD
Citação: TETRAHEDRON. - Vol. 64, n. 49 (DEC 1 2008), p. 11144-11149
Resumo: The acylation of bioactive primaquine-based imidazolidin-4-ones was studied using N-chi-Boc-protected glycine as acylating agent. Two synthesis routes, eight different coupling methods and seven distinct solvents were compared. Mild carbodiimide-based couplings on high dielectric constant solvents such as DMF or MeCN increased acylation yields, whereas alcohols inhibited carbodiimide-mediated acylations to take place. Achievement of the synthetic goals was limited by the size of the imidazolidin-4-one ring substituents R-1, R-2 and R-3, but resort to MW-assisted synthesis allowed overcoming such obstacle, though with very modest reaction yields. All reactions involving a Boc-protected amino acid were regioselective, independent of reaction conditions employed. In contrast, regioselective acetylation of the imidazolidin-4-ones could only be achieved by resort to very mild coupling procedures. (C) 2008 Elsevier Ltd. All rights reserved.. - Fundacao para a Ciencia e a Tecnologia (FCT, Portugal) ; PTDC/QUI [65142/ 2006]; SFRH/BD [17754/2004]; CIQUP ; CECF ; CEM Corporation (USA) ; QLabo (Portugal) ; CEM DiscoverSUPTM/SUP system. - Thanks are due to Fundacao para a Ciencia e a Tecnologia (FCT, Portugal) for financial Support through Project PTDC/QUI/65142/ 2006. N.V. thanks FCT for Ph.D.grant SFRH/BD/17754/2004. P.G. and R.M. thank FCT for financial support to CIQUP and CECF, respectively. Thanks are also due to CEM Corporation (USA) and QLabo (Portugal) for providing a CEM DiscoverSUPTM/SUP system for a trial period.
URI: http://hdl.handle.net/10451/21673
DOI: http://dx.doi.org/10.1016/j.tet.2008.09.058
ISSN: 0040-4020
Aparece nas colecções:FF - Produção Científica 2000-2009

Ficheiros deste registo:
Não existem ficheiros associados a este registo.


FacebookTwitterDeliciousLinkedInDiggGoogle BookmarksMySpace
Formato BibTex MendeleyEndnote Degois 

Todos os registos no repositório estão protegidos por leis de copyright, com todos os direitos reservados.