engleski

Synthesis of rhodanine derivatives via Knoevenagel condensation in deep eutectic solvents

The development of pharmaceuticals and drug production has led to an increase in synthesis of compounds that have a positive effect on human health. Nowadays, attention is increasingly being drawn to the green synthesis technologies. One of the green approaches in synthesis is usage of deep eutectic solvents (DESs) since those solvents are easily synthesized from biodegradable and environmentally benign components. Also DESs have low toxicity, high availability, low inflammability, high recyclability, low volatility and low price [1]. In this research deep eutectic solvents (DESs) are used as reaction media and catalyst. Among the many desired compounds that are synthesizing today, rhodanine derivatives are compounds that have been increasingly synthesized due their significant biological activities such as antibacterial, antifungal, antiviral, antimalarial, insecticidal, herbicidal, antitumor, anti-inflammatory and cardiotonic activities. It has been reported that rhodanine derivatives can potentially be used in the treatment of diabetes, obesity, Alzheimer’s disease, cystic fibrosis, thrombocytopenia, cancer, sleep, mood and central nervous system disorders as well as chronic inflammation [2]. In this work Knoevenagel condensation of salicylaldehyde and rhodanine in 20 different DESs at 80°C is performed in order to find the best reaction media. DESs are based on choline chloride (ChCl) as hydrogen bond acceptor and 20 other components in role of hydrogen bond donors like urea, carboxylic acids, sugars or amides. Product was obtained in all reaction media, but in different yields. The best reaction media was proven to be ChCl:acetamide (ChCl:A, 1:2) with highest yield of 96.3 % followed by ChCl:malonic acid (ChCl:MA, 1:1) with yield of 91.1 %.

rhodanine ; synthesis ; deep eutectic solvents ; green solvents

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