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Communication | Special issue | Vol 56, No. 1-2, 2002, pp.73-80
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)32
Synthesis of Heterocycle-annulated Azulenequinone Derivatives

Hidetsugu Wakabayashi,* Seiichi Matsumaru, Teruo Kurihara, and Masafumi Yasunami

*Department of Chemistry, Faculty of Science, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan


Treatment of 2-methoxyazulene (2) with 4.2 equiv. of bromine in aqueous THF at 0°C for 1 h afforded 3-bromo-2-methoxy-1,5- (1a) and -1,7-azulenequinone (1b) in a 16:1 ratio. Reaction of 1a with o-aminobenzenethiols gave 12H-azuleno[1,2-b]benzo[e][1,4]thiazine-7,11-dione derivatives (6a,b).