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  • Title: Benzo[cd]azulene skeleton: azulene, heptafulvene, and tropone derivatives.
    Author: Aumüller IB, Yli-Kauhaluoma J.
    Journal: Org Lett; 2009 Dec 03; 11(23):5363-5. PubMed ID: 19904921.
    Abstract:
    Due to our interest in protein kinase modulating compounds, we developed syntheses for benzo[cd]azulenes. By using very common catalysts and reagents, such as t-BuOK, HCl, and mCPBA, the commercially available guaiazulene is converted in three steps into tricyclic tropone derivatives. Electrophilic aromatic substitution reactions of guaiazulene proceed without a catalyst. Complex one-pot reactions convert 1'-hydroxyalkyl azulenes into tricyclic heptafulvenes, and finally, the mild oxidant mCPBA cleaves the semicyclic C horizontal lineC double bonds to furnish tropones.
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