Heterocyclic systems containing bridgehead nitrogen atom: Synthesis and biological activity evaluation of <i>s</i>-triazolo[3,4-<i>b</i>] [1,3,4]thiadiazoles,<i>s</i>-triazolo[3,4-<i>b</i>] [1,3,4]thiadiazines and <i>s</i>-triazolo [3',4':2,3] [1,3,4 ]thiadiazino[5,6-<i>b</i>]quinoxaline

Abstract

The condensation of 3-<i>p</i>-(<i>t</i>-butylphenyl)-4-amino-5-mercapto-<i>s</i>-triazole <b>1</b>, independently, with chloroacetic acid, α-haloketones, benzoin, 2,3-dichloroquinoxaline, aromatic carboxylic acids, carbon disulphide and aromatic carboxaldehydes furnishes in one step the cyclic products, 3-<i>p</i>-(<i>t</i>-butylphenyl)-7<i>H-s</i>-triazolo[3,4-<i>b</i>][1,3,4]thiadiazin-6(5<i>H</i>)-one <b>2</b>, 6-aryl-3-<i>p</i>(

<i>t</i>-butylphenyl)-7<i>H</i>-<i>s</i>-triazolo[3,4-<i>b</i>][1,3,4]thiadiazine <b>3</b>, 3-<i>p</i>-(<i>t</i>-butylphenyl)-6,7-diphenyl-5<i>H</i>-<i>s</i>-triazolo[3,4-<i>b</i>][1,3,4] thiadiazine <b>4</b>, 3-<i>p</i>-(<i>t</i>-butylphenyl)-5<i>H-s</i>-triazolo[3' ,4' :2,3][1,3,4] thiadiazino[5,6-<i>b</i>] quinoxaline <b>5</b>, 3-<i>p</i>-(<i>t</i>-butylphenyl)-6-aryl-<i>s-</i>triazolo[3,4-<i>b</i>][1,3,4] thiadiazoles <b>6</b>, 3-<i>p</i>-(<i>t</i>-butylphenyl)-<i>s</i>-triazolo[3,4-<i>b</i>][1,3,4]thiadiazole-6(5<i>H</i>)-thione <b>7</b> and 6-aryl-5,6-dihydro-3-<i>p</i>(<i>t</i>-butylphenyl)-<i>s</i>-triazolo[3,4-<i>b</i>] [1,3,4] thiadiazoles <b>8</b> respectively. The structures have been established on the basis of elemental analysis and spectral data. The antibacterial and antifungal activity of some of the compounds have also been evaluated.