New chemical entities encompassing 1,2,3-triazole and quinazolinones (7a-h) have been synthesized starting from 4-hydroxy benzaldehyde (1) in three steps involving the addition of propoxyl bromide (2) , iodine/dimethyl sulfoxide catalyzed condensation of anthranilamide (4) and finally 'Click' reaction with various phenylazides (6a-h). Several analogs have been synthesized in excellent yields and fully characterized by using 1 H NMR, IR and Mass spectroscopic methods and they were superior in accordance with the proposed structures.