Synthesis of N-cyclohexyl-6-(5-aryl-2-furyl)imidazo [2,1-b][1,3,4]thiadiazol ([1,3]thiazol)-5-amine derivatives

Substances that contain imidazole fragment show a wide range of biological activity. The imidazole moieties are widely presented in the molecules of alkaloids (caffeine, pilocarpine), coenzymes (flaviniden nucleotide), essential amino acids (histidine), tranquilizers (mebicar), hormones analogues (Mercazolil), antimetabolites (6-mercaptopurine). Lots of imidazole derivatives are found among the drugs such as naftisin, galazolin, oxfendazole, mycozolone, etymizole, clonidine etc. Likewise, drugs that contain arylfuran unit are being used in therapeutic practice, especially in the treatment of genetic diseases and in the development of drugs for the treatment of tobacco dependence. In the last case, in order to reduce the need for nicotine and eliminate the symptoms of withdrawal from smokers who decide to quit smoking. Therefore, merging of imidazole and arylfuran fragments is very interesting in terms of medicinal chemistry. On the other hand, the attention of chemists is attracted to multicomponent reactions based on isocyanides which are characterized by high reactivity and a large variety of chemical transformations. One of such transformations is three-component Groebke method, where, aldehyde with the derivative of aminothiazole and isonitrile react. At the initial stage of research, one isonitrile was selected. It was cyclohexylizonitrile. It is convenient in operation and it is easy to synthesize and purify by distillation, unlike other isocyanides. Through the three-component cycloaddition of 5-arylfurfurals with 2-aminothiazole derivatives and cyclohexylisonitrile under the Groebke reaction conditions a series of new substituted N-cyclohexylimidazo[2,1-b][1,3,4]thiadiazol-5-amines and N-cyclohexylimidazo [2,1-b][1,3]thiazol-5-amine with arylfuran moieties were obtained. Keywords: furan derivatives, arylfurfurals, cycloadditions, N-cyclohexylimidazo[2,1- b ][1,3,4]thiadiazol(thiazol)-5-amines.