2-Methyloxazolo[4,5-b]phenazine (2) was obtained through the cyclocondensation of 3-aminophenazin-2-ol (1) with acetic anhydride. Oxazolophenazine derivatives (3a-d) were synthesized by oxidatively adding 3-aminophenazin-2-ol (1) to aromatic aldehydes. The addition of 3-aminophenazin-2-ol (1) to activated acrolein resulted in the formation of the 2-methylene-2H-[1,4]oxazino[2,3-b]phenazine (5). Alkylation and subsequent cyclization of aminophenazin-2-ol (1) using phenacyl bromide and/or ethyl acetochloroacetate produced 2-phenyl-4H-[1,4]oxazino[2,3-b]phenazine (7) and 3-acetyl-2H-[1,4]oxazino[2,3-b]phenazin-2-one (9), respectively. The cyclocondensation of aminophenazin-2-ol 1 with cyanoacetamide led to the synthesis of 2-amino-1H-pyrrolo[2,3-b]phenazine-3-carbonitrile (10). 2H-[1,4]oxazino[2,3-b]phenazin-2-one (11) was generated through the alkylation of aminophenazin-2-ol (1) in pyridine followed by cyclization. The antifungal activity of oxazine derivatives (9) , (10), and pyrrole derivatives (11) was evaluated against two fungal species, Candida albicans and Aspergillus niger. The tested compounds exhibited varying degrees of antifungal activity against the two fungal strains.