Please use this identifier to cite or link to this item:
https://hdl.handle.net/10216/82026
Author(s): | Nuno Vale Joana Matos Rui Moreira Paula Gomes |
Title: | Amino acids as selective acylating agents: regioselective N-1-acylation of imidazolidin-4-one derivatives of the antimalarial drug primaquine |
Issue Date: | 2008 |
Abstract: | 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. |
Subject: | Química Chemical sciences |
Scientific areas: | Ciências exactas e naturais::Química Natural sciences::Chemical sciences |
URI: | https://repositorio-aberto.up.pt/handle/10216/82026 |
Document Type: | Artigo em Revista Científica Internacional |
Rights: | openAccess |
License: | https://creativecommons.org/licenses/by-nc/4.0/ |
Appears in Collections: | FCUP - Artigo em Revista Científica Internacional |
This item is licensed under a Creative Commons License