2,7-Diarylmethylene-cycloheptanone, Hydrazonoyl Chlorides and Heterocyclic Amines as Precursors for Synthesis of Bioactive New Fused Cycloheptapyrimidine Derivatives

摘要

A series of novel cyclohepta[1,2-d][1,2,4] triazolo[4,3-a] pyrimidines was prepared by reaction of 9-arylmethylene-cycloheptapyrimidine-2-thione with hydrazonoyl halides in dioxane in the presence of triethylamine. Also, a series of fused cycloheptapyrimidines was synthesized via reaction of 2,7-diarylmethylene-cycloheptanone with heterocyclic amines. The products 14a-c of the latter reaction were used as starting materials since they contain an olefinic exocyclic C=C and endocyclic C=N bonds. 1,3-Dipolar cycloaddition reaction of these products with hydrazonoyl halides in benzene in the presence of triethylamine afforded novel spiropyrazolines. All the above reactions proceeded site and regio-selectively, and the structures of the products were established based on both elemental and spectral analysis data (IR, H-1 NMR, MS). In addition, the biological activity of some of the new products was evaluated and the results obtained revealed medium to high activity against some bacteria and fungi species.