Romanian Society of Pharmaceutical Sciences
 

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HETEROCYCLES 41. SYNTHESIS AND CHARACTERISATION OF NEW THIAZOLE β-AMINO ACIDS AND β-AMINO ESTERS

DENISA LEONTE1, LÁSZLÓ CSABA BENCZE2, RÓBERT TŐTŐS2, VALENTIN ZAHARIA1*

1.“Iuliu Haţieganu” University of Medicine and Pharmacy, Department of Organic Chemistry, 41 Victor Babeş Street,
Ro-400012 Cluj-Napoca, Romania
2.“Babeș-Bolyai” University, Faculty of Chemistry and Chemical Engineering, Biocatalysis and Biotransformation Research Group, 11 Arany János Street, Ro-400028 Cluj-Napoca, Romania

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Being aware of the biological potential, low toxicity as well as biocompatibility of both amino acids and naturally occurring heterocycles, the aim of this study was the synthesis and characterization of new β-amino acids and their ethyl esters bearing the thiazole core. The thiazole β-amino acids were obtained with 52 - 68% yields, by applying a synthetically convenient modification of the Rodionov reaction, consisting in the condensation of 2-arylthiazole-4-carbaldehydes with malonic acid and ammonium acetate. The obtained β-amino acids were converted into ethyl carboxylates by a single-step procedure, involving the activation of the carboxyl group by treatment with thionyl chloride. The synthesized compounds were purified and characterized by melting point, 1H NMR, 13C NMR and mass spectrometry.