Synthesis and antifungal activity of novel polyheterocyclic compounds containing fused 1,2,4-triazine moiety

3-Amino-4-(4-chlorophenyl)-7-hydrazino-8H-pyrazolo[4,3-e][1,2,4]triazolo[1',5'-a]pyridine-5-carbonitrile (4) was synthesized from 4-(4-chlorophenyl)-1,6-diamino-2-oxo-1,2-dihydropyridine3,5-dicarbonitrile (1). Reaction of 4 with alpha,beta-bifunctional compounds gave pyrazolotriazinotriazolopyridines (8-14). The behavior of 4 towards condensation reactions with indole-2,3-dione in different media gave different products 15-16. Acetylation of 16 led to different products depending on the reaction conditions. Structures of the products have been deduced from analytical and spectral data (UV, IR, H-1 NMR, C-13 NMR and mass spectra). Some of the products were screened for antifungal activity.