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

Abstract

3-Amino-4-(4-chlorophenyl)-7-hydrazino-8H-pyrazolo[4,3-e][1,2,4] triazolo[1̀,5̀-a]pyridine-5-carbonitrile (4) was synthesized from 4-(4-chlorophenyl)-1,6-diamino-2-oxo-1,2-dihydro-pyridine-3,5-dicarbonitrile (1). Reaction of 4 with α,β-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, 1H NMR, 13C NMR and mass spectra). Some of the products were screened for antifungal activity. © ARKAT USA, Inc.