Tropolones & Azulenes

Azulenes are the collective term for compounds which have a specific structure of ring-fused unsaturated seven-membered and five-membered rings, and they are named after Azur which is blue in Arabic. Three practical manufacturing methods are as followed:
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 between tropone derivatives which substitutes halogen, methoxy, or tosyloxy groups at the 2 position, and the 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 with oxazulanones and enamines.
Hinokitiol which is well known tropolone derivative has antibacterial effect. Also colchicine which is alkaloid and contains tropolone ring shows strong antitumor effect. Tropolone compounds have possibilities in pharmaceutical field, especially for anticancer drugs.

Tropolones

Azulenes

Others

Tropolones

C0380 C0380 H0142 H0142 P0542 P0542
T0606 T0606 T1574 T1574
C0380 Colchicine (contains 5% Ethyl Acetate at maximum)
H0142 Hinokitiol
P0542 Purpurogallin
T0606 Tropolone
T1574 Tropolone Tosylate

Azulenes

A0634 A0634 G0228 G0228
A0634 Azulene
G0228 Guaiazulene

Others

M1188 M1188 I0657 I0657
M1188 3-(Methoxycarbonyl)-2H-cyclohepta[b]furan-2-one
I0657 5-Isopropyl-3-(methoxycarbonyl)-2H-cyclohepta[b]furan-2-one

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
M. Yamato, Yakugaku Zasshi, 1992, 112, 81.
K. Takase, M. Yasunami, Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem., Jpn.), 1981, 39, 1172.
T. Asao, S. Ito, Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem., Jpn.), 1996, 54, 2.


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