Reactions of Acridine

Reactions of Acridine involve electrophilic substitution, oxidation, and reduction processes important in pharmaceuticals and dyes.

Reactions of Acridine

1. Electrophilic Substitution (EAS)

   • Preferred at positions 2 and 7 (central ring).
   • Examples:
     • Nitration: 2-nitroacridine (HNO₃ + H₂SO₄)
     • Halogenation: Br₂ → 2-bromoacridine

2. Nucleophilic Substitution (NAS)

   • C-9 and neighboring positions can undergo substitution when activated (e.g., by halogen + EWG).

3. Reduction

   • H₂, Pd/C → dihydro- or tetrahydroacridine
   • Strong reducing agents can open or saturate the ring.

4. N-Oxide Formation

   • m-CPBA → acridine N-oxide: enhances nucleophilic reactivity of the ring.

5. Basicity and Salt Formation

   • Nitrogen can be protonated or alkylated:
     • Forms acridinium salts, useful in dyes and photochemistry.

6. Photochemical Properties

   • Acridine is fluorescent.
   • Used in dyes, intercalating agents (DNA), drugs (acridine orange, proflavine).

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