[1,2,4]Triazolo[4,3-c]quinazolines bearing p-bromophenyl or 5-bromothiophen-2-yl moiety at position 5 have been synthesized by cyclocondensation of the corresponding 4-hydrazinoquinazolines with ortho esters in boiling ethanol or glacial acidic acid. The synthesized tricyclic derivatives represent valuable intermediates for design of fluorophores and biologically active compounds. The possibility of modifying 5-(4-bromophenyl) derivatives by cross-coupling reaction has been demonstrated.