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Synthesis 2024; 56(09): 1429-1437
DOI: 10.1055/a-2231-4922
DOI: 10.1055/a-2231-4922
paper
Solvent-Free Efficient Synthesis of New 4-Thiazolidinones with a Fructose Scaffold through a Microwave-Assisted Cascade Multicomponent Reaction
This work was supported by grants from Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET, Buenos Aires, Argentina, PIP11220210100251CO01-CONICET) and UNS (Universidad Nacional del Sur, Bahía Blanca, Argentina, PGI24Q/102). A fellowship from CONICET to F.L. is acknowledged.
Abstract
Using a chemoselective, sustainable and highly efficient method, new 4-thiazolidinones and 1,4-thiazepan-3-ones substituted with a glycosidic residue derived from d-fructose were synthesized. Microwave-assisted cascade multicomponent reaction under solvent-free conditions gave very good yields in short reaction times, which was followed by a nontoxic purification method of one of the diastereomers by precipitation–centrifugation. The new purified compounds isolated as diastereomers were evaluated as factor Xa (FXa) inhibitors.
Key words
4-thiazolidinones - 1,4-thiazepan-3-ones - carbohydrates - chemoselectivity - multicomponent reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2231-4922.
- Supporting Information
Publication History
Received: 17 November 2023
Accepted after revision: 18 December 2023
Accepted Manuscript online:
18 December 2023
Article published online:
12 February 2024
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