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Non-benzenoid Aromatic Compounds [Chemical Structural Class]
Azulene, which has a specific structure of ring-fused unsaturated seven-membered and five-membered rings, is a typical non-benzenoid aromatic compound. Whereas naphthalene or other hydrocarbon compounds are generally colorless, azulene, a structural isomer of naphthalene, is dark blue, and the name comes from the Spanish word azul, meaning "blue". Three practical manufacturing methods have been known so far as follows:The first method, which was developed by Ziegler and Hafner, is a reaction of ring-opened pyridinium salts or pyrylium salts with cyclopentadienides. The second one, which was developed by Nozoe and Seto et al. is a reaction of tropone derivatives bearing halogen, methoxy, or tosyloxy groups at the 2 position and active methylene compounds, such as cyanoacetates and malonates, in the presence of base. The last method, which was developed by Yasunami and Takase et al., is a reaction of oxaazulanones with enamines.
Tropolone derivatives are also classified as non-benzenoid aromatic compounds. Hinokitiol, a typical tropolone compound, has been known to exhibit an antibacterial effect. Also colchicine, an alkaloid compound with a tropolone ring, shows strong antitumor effects. Thus, tropolone compounds have possibilities in the pharmaceutical field, especially for anticancer drugs.
Literature
- 1)K. Ziegler, K. Hafner, Angew. Chem. 1955, 67, 301.
- 2)T. Nozoe, S. Seto, S. Matsumura, T. Asano, Proc. Japan Acad. 1956, 32, 339.
- 3)P. W. Yang, M. Yasunami, K. Takase, Tetrahedron Lett. 1971, 4275.
- 4)Reviews:
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