Dibenzosuberenone


5-Dibenzosuberenone is an organic chemical with use in drug synthesis. Chemically speaking, the structure can be described as a benzophenone moiety bonded through an ethylene bridge into a seven membered ring. In contrast to dibenzosuberone, dibenzosuberenone does not contain any sp3 hybridized bonds.

Applications

Dibenzosuberenone predominantly has uses in the synthesis of tricyclic antidepressants.
  1. Citenamide
  2. Cyclobenzaprine
  3. Cyproheptadine
  4. Decitropine
  5. Demexiptiline
  6. Dinorcyclobenzaprine:
  7. Dizocilpine
  8. Intriptyline
  9. Mariptiline
  10. Norcyclobenzaprine
  11. Norcyproheptadine
  12. Octriptyline
  14. Protriptyline
  15. Zosuquidar
#
  1. CPG 146, CPG 147, CPG 148, CPG 186, CPG 191, CPG 264 :

Synthesis

Dibenzosuberenone is made from dibenzosuberone by dehydrogenation.
In an alternative method dibenzosuberone is halogenated with NBS; dehydrohalogenation then also furnishes the target molecule. In an older document molecular bromine was used under irradiation. This gave a 70-90% yield of product.
2-Carboxybenzaldehyde and hydroxyphthalide exist together in a tautomeric equilibrium. Wittig reaction to this forms predominantly -2-stilbenecarboxylic acid . It is important to mention that the Z-isomer is indeed the favored product of this step and not the trans-isomer. Cyclization of the carboxylic acid in polyphosphoric acid then also forms dibenzosuberenone.