Ionic Liquid as a Green Media for the One-Pot Synthesis of New α- Thiazolodepsipeptide Derivatives via a Four-Component Reaction

Author(s): Ashraf S. Shahvelayati, Akram Ashouri, Akram S. Delbari.

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 2 , 2016

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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.

Keywords: Depsipeptide, passerini reaction, phenacyl bromide, tandem reaction, thiourea carboxylic acid.

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Article Details

VOLUME: 13
ISSUE: 2
Year: 2016
Page: [100 - 106]
Pages: 7
DOI: 10.2174/1570178613666151112224143
Price: $65

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