STUDIES ON THE VILSMEIER-HAACK REACTION .11. NOVEL HETEROCYCLO-SUBSTITUTED THIOQUINOXALINONE DYES

Novel azo sulfa drugs of 3-methyl-1-[4-(substituted sulfamoyl)phenylazo]-2(1H)-quinoxalinethiones were synthesized and found to undergo diformylation reaction with Vilsmeier reagent giving the 3-(3-aminoacrylalde-hyde-substituted)-1-(4-sulfamoylphenylazo)-2(1H)-quinoxalinethione dyes 4-6. Reaction of 4, 5, and/or 6 with proper reagents afforded the corresponding morpholinyl, piperidinyl, 4-piperazinyl-1H-pyrazol-4-yl, 1-phenyl-1H-pyrazol-4-yl, 4-isoxazoyl, and 5-amino-1H-pyrazol-4-yl substituted 2(1H)-quinoxalinethione derivatives at the 3-position of the quinoxaline moiety. The structures of these novel compounds were confirmed by elemental analysis, IR and H-1 NMR spectroscopy and screened in vitro for antibacterial (Gram-positive and Gram-negative bacteria) and antifungal activities.