Abstract Condensation of 2-hydrazino-4 (3H)-quinazolinone (1) with bielectrophilic reagents gives the corresponding triazoloquinazolines 8, the structures of which were established by selective synthesis through deamination of their N-amino derivatives. The synthesis of methyl-substituted derivatives of these angular tricyclic systems and their linear isomers was also achieved starting with 3-methyl-and 1-methyl-2-hydrazino-quinazolinone.