Organic Letters 2009-12-03

Benzo[cd]azulene skeleton: azulene, heptafulvene, and tropone derivatives.

Ingo B Aumüller, Jari Yli-Kauhaluoma

文献索引：Org. Lett. 11(23) , 5363-5, (2009)

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摘要

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.

相关化合物

  • 甘菊蓝
  • 环庚三烯酮

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