Title:Ionic Liquid as a Green Media for the One-Pot Synthesis of New α- Thiazolodepsipeptide Derivatives via a Four-Component Reaction
VOLUME: 13 ISSUE: 2
Author(s):Ashraf S. Shahvelayati, Akram Ashouri and Akram S. Delbari
Affiliation:Department of Chemistry, Yadegar-e-Imam Khomeini (RAH) Shahre-rey Branch, Islamic Azad University, Tehran, Iran.
Keywords:Depsipeptide, passerini reaction, phenacyl bromide, tandem reaction, thiourea carboxylic acid.
Abstract:Background: A depsipeptide is a molecule that has both peptide and ester linkages in proximity in the
same amino acid-containing small molecule or chain. Many depsipeptides show very promising biological
activities, including anticancer, antibacterial, anticancer, antiviral, antifungal, anti-inflammatory,
and anti-clotting or anti-antherogenic properties.
The aim of this paper is to apply ionic liquid as a green media for the synthesis of new α-thiazolodepsipeptide derivatives
via a four-component reaction.
Methods: Thiazole-containing depsipeptides were produced easily in one step by a four-component Condensation/ Passerini
tandem reaction of thiourea carboxylic acid derivatives, phenacyl bromides, ketones and isocyanides in 1-methyl-3-
pentylimidazolium bromide as new solvent.
Results: As shown in Scheme 1, the reaction of thiourea carboxylic acid 1, phenacyl bromide or its derivatives 2, alkyl
isocyanides 3 and ketones 4 in an ionic liquid at 50°C produce depsipeptide derivatives 5 in good yield. The products
were characterized by 1H NMR, 13C NMR, Mass ,and IR spectroscopy. This reaction carried out based on combination of
cyclization and passerini reactions.
Conclusion: In summary the reaction of thiourea carboxylic acid, phenacyl bromide or its derivatives, alkyl isocyanides
and ketones in ionic liquid at 50°C produce depsipeptide derivatives in good yields. The advantage of the present procedure
is that all four substrates were mixed in ionic liquid as a one-pot reaction without any catalyst and without the need
for separation of intermediates.
