The scientific work is devoted to the development of new approaches to synthesis of heterocycles with arylfuran fragments, for this purpose 5-arylfuran-2-carbaldehydes and 3-(5-aryl-2-furyl)acroleins were used as starting reagents in multicomponent transformations.
The limits of the application of: the Radziszewski reaction (preparation of 2,4,5-triarylimidazoles with an arylfuran moiety), Hantzsch reaction (synthesis of substituted 4-(5-aryl-2-furyl)-1,4-dihydropyridines), Biginelli reaction (synthesis of 4-[5-(aryl-2-furyl]-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidines), Groebke reaction (preparation of imidazo[2,1-b][1,3,4]thiadiazole and imidazo[2,1-b]thiazole derivatives), Ugi–Diels-Alder reaction (interaction of isonitrile with unsaturated acid, amines (aromatic or aliphatic) and 3-(5-aryl-2-furyl)acroleins) were disclosed. Reaction of substituted 5-arylfuran-2-carbaldehydes with dimedone and 6-aminouracil has been studied and as a result 5-(5-aryl-2-furyl)-5,8,9,10-tetrahydropyrimido[4,5-b]quinoline-2,4,6-trions have been obtained. It has been established that 5-arylfuran-2-carbaldehydes reacts with a double excess of dimedone and ammonium acetate to form 3,3,6,6-tetramethyl-9-(5-aryl-2-furyl)-3,4,6,7,9,10-hexahydroacridine-1,8-(2H,5H)-diones. A method for the synthesis of 4,6-disubstituted 2-amino-3-cyanopyridines by four-component cyclization (5-arylfurfurals, aromatic ketone, malonodinitrile and ammonium acetate) has been developed. It has been shown that 5-arylfurfurals can be used in design of 2-amino-7,7-dimethyl-5-oxo-4-(5-aryl-2-furyl)-5,6,7,8-tetrahydro-4H-chromen-3-carbonitriles. Using three-component cyclization, methods for the synthesis of 7-amino-5-[5-aryl-2-furyl]-3,4-dihydro-1H-isothiochromene-6,8-dicarbonitrile-2,2-dioxides derivatives have been developed. In this transformation 5-arylfurfurals, malonodinitrile and 3-oxotetrahydro-2H-thiopyran-1,1-dioxide were used as reagents. A general approach for design of hybrid structures with fragments of thiazolo[3,2-b][1,2,4]triazol-6-ones and imidazo[2,1-b][1,3]thiazol-3-ones has been developed. For this purpose three-component reactions of 5-arylfuran-2-carbaldehydes or 3-(5-aryl-2-furyl)acroleins with chloroacetic acid and mercaptoazoles were used.
