Regioselective synthesis of novel N-aminotriazolophanes

Bis-[4-amino-1,2,4-triazoles] were prepared by fusion of dibasic acids and thiosemicarbazide by condensation of aromatic acid hydrazides with hydrazine hydrate and carbon disulphide. Regioselective alkylation of these bis-[4-amino-1,2,4-triazoles] with 1,ω-dihaloalkanes in the presence of potassium hydroxide in aqueous methanol afforded novel N-aminotriazolophanes. The stereochemistry and antibacterial activity of these N-aminotriazolophanes were studied. In the case of the triazolophanes 5h , 8d , and 8f , both N-NH 2 groups were observed trans to each other, whereas for case of other triazolophanes both N-NH 2 groups were observed cis to each other.Key words: 4-amino-1,2,4-triazole, 1,ω-dihaloalkane, S-alkylation, regioselective, N-aminotriazolophanes.