Novel bridgehead nitrogen bisheterocyclic systems: Synthesis, stereochemistry and antimicrobial activity of <i>p-bis</i>[2<i>H</i>, 5<i>H</i>-4-oxo-thiazol-3-yl]phenylenes and <i>p-bis</i>[<i>cis</i>-5<i>H</i>-3,3a-dihydropyrazolo[3,4-<i>d</i>]thiazol-6-yl]phenylenes

Abstract

The facile synthesis of <i>p-bis</i>[<i>cis</i>-3,3a-dihydro-5<i>H</i>-pyra­zolo[3,4-<i>d</i>]thiazol-6-yl]phenylenes <b>4</b> has been achieved by the condensation of <i>p-bis</i>[4-substituted phenylimine]phenylenes <b>1</b> with thioglycollic acid in toluene, using Dean-Stark water separator, to give <i>p-bis</i>[2H,5<i>H</i>-4-oxo-2-(<i>p</i>-substituted phenyl)­thiazol-3-yl]phenylene <b>2</b>, which on condensation with aryl­aldehydes furnishes 5-arylidene derivatives <b>3</b> followed by treatment with 2,4-dinitrophenylhydrazine. The antibacterial and antifungal activities of some of the compounds have also been evaluated.