Benzoxazines have been widely used in many fields, such as the aerospace, electronics, and automotive industries; however, these resins exhibit nonrecyclable nature and limited strength (for their brittleness). Introducing reversible covalent bonds in benzoxazines is expected to address these issues. Herein, two-benzene-ringconjugated Schiff-base benzoxazine was successfully synthesized using a designed strategy. Using this strategy, possible side reactions, such as the transimination of the Schiff-base, were prevented when preparing the target product via the traditional Mannich reaction. The cured benzoxazine could chemically degrade under acidic conditions and it undergoes controllable degradation when the temperature, acidity, and solvent are changed. The synthesized benzoxazine forms noticeable liquid crystals