2-(Cyclopropylamino)-5-(4-methoxybenzylidene)thiazol-4(5<i>H</i>)-one

• Published in: Molbank
• Main Authors: Ivan Sydorenko, Serhii Holota, Andrii Lozynskyi, Yulian Konechnyi, Volodymyr Horishny, Andriy Karkhut, Svyatoslav Polovkovych, Olexandr Karpenko, Roman Lesyk
• Format: Article
• Language: English
• Published: MDPI AG 2022-10-01
• Subjects: multicomponent reactions; 4-thiazolidinones; rhodanine; cyclopropylamine; antimicrobial activity
• Online Access: https://www.mdpi.com/1422-8599/2022/4/M1478

Multicomponent reactions effectively contribute to modern organic and medicinal chemistry. 4-Thiazolidinone core and cyclopropyl moiety are important structural motifs for design of potential biologically active molecules. In the present paper, the convenient step-economy and cost-effective synthesis of 2-(cyclopropylamino)-5-(4-methoxybenzylidene)thiazol-4(5<i>H</i>)-one (<b>2</b>) is described based on the application of the MCR methodology. The proposed approach includes direct one-pot interaction of 2-thioxothiazolidin-4-one (rhodanine), 4-methoxybenzaldehyde with cyclopropylamine which was used in 10% excess compare to other reagents. The structure of synthesized compound <b>2</b> was confirmed using ¹H, ¹³C, 2D NMR, LC-MS, IR and UV spectra. The presence of prototropic amino/imino tautomerism for synthesized compound <b>2</b> was observed based on spectral analysis data. Screening of antimicrobial activity against 12 strains of Gram-positive and Gram-negative bacteria, as well as yeasts, was performed for synthesized derivative <b>2.</b>