Synthesis and antibacterial activity of fused 1, 2, 4-triazolo[4, 3-a]quinoxaline and oxopyrimido[2', 1':5, 1]-1, 2, 4-triazolo[4, 3-a]quinoxaline derivatives.

Abstract

A new series of potential antibacterial agents having tricyclic 1, 2, 4-triazolo-[4, 3-a] quinoxaline fused with one or more heterocyclic rings was synthesized via several routes. The tricyclic 1-amino-4-chloro-1, 2, 4-triazolo[4, 3-a] quinoxaline (2 ) and tetracyclic 1, 6-diamino-bis-1, 2, 4-triazolo[4, 3-a:3, 4-c] quinoxaline (3) were synthesized from 2, 3-dichloroquinoxaline (1) with two or four equivalents of thiosemicarbazide, respectively. Compound 2 was allowed to react with different aldehydes, alkoxides, cyclic amines, phenyl isothiocyanate, and t-butyl isocyanate to afford the corresponding quinoxaline derivatives. Moreover, compound 2 reactedwithhydrazine hydrate to give compound 4 which was cyclized by carbondisulfide inalcoholic potassium hydroxide to give the tetracyclic compound 5. Compound 2 was subjected to another cyclocondensation reaction using diethyl ethoxymethylene malonate (DEMM), dimethyl acetylenedicarboxylate (DMAD), and ethyl cyanoacetate to give the tetracyclic compounds 18, 20, and 21, respectively. All the synthesized compounds were evaluated in vitro for antibacterial activity; compounds 18 and 20 were found to display the greatest antibacterial activities. Structural identification was provided by elemental analyses, IR, and (1)H-NMR spectroscopy.