SYNTHESIS OF NEW 4-PHENYL-1-(3,4,5-TRIMETHOXYPHENYL)-1H-IMIDAZOLE-2-THIOLDERIVATIVES

Imidazoles are a large group of compounds that play important role in organic and medicinal chemistry. The specific structure of the imidazole ring with desirable electrophilicity makes its compounds very versatile for many biological applications. Derivatives of imidazoles attract considerable interest in the field of organic synthesis due to their wide spectrum of biological activity – these compounds contribute to various catalysis in enzymatic and endocytosis processes also this structures are known to have a wide variety of biological activities including antidiabetic, antioxidant, anti-amoebic, antihelmintic antibacterial, antimycobacterial, anti-inflammatory, antitumor, antidiabetic, antiviral, and antifungal activities [1−3].

In this study, 3,4,5-trimethoxyaniline () upon reaction with phenacyl bromide in methanol at room temperature for 2h formed the target 1-phenyl-2-((3,4,5-trimethoxyphenyl)amino)ethan-1-one (). To obtain compound , α-amino ketone reacted with potassium thiocyanate in diluted HCI. The reactions afforded imidazole-2-thione , which can exist in the tautomeric form.We found that the reaction of compound with methyl bromoacetate in ethanol, in the presence of potassium carbonate, occurred uniquely to give the product of S-alkylation – methyl 2-((4-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-imidazol-2-yl)thio)acetate (). The obtained methyl ester was transformed into hydrazide using hydrazine monohydrate in 2-propanol (Fig. 1). Condensation of compound with aromatic aldehydes in propan-2-ol led to the formation of N’-benzylidene hydrazides 6a-f. The structures of the obtained compounds 6a-f were confirmed by the data of the \(^{1}\)H, \(^{13}\)C NMR and FT-IR spectroscopy and elemental analysis.