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Paper | Special issue | Vol 76, No. 2, 2008, pp.1133-1140
Published online, 22nd May, 2008
DOI: 10.3987/COM-08-S(N)71
Synthesis of 1,2-Azulenequinone Derivatives by Bromine-Oxidation

Hidetsugu Wakabayashi,* Osamu Irinamihira, Satoshi Shibata, Teruo Kurihara, Yuzuru Uchiyama, Akira Ohta, and Kunihide Fujimori

*Department of Chemistry, Graduate School of Material Science, Josai University, Sakado, Saitama 350-0295, Japan

Abstract

Treatment of 2-hydroxyazulene (1a) with 3 equiv. of C5H5N·HBr3 in aqueous THF-AcOH at 0 oC for 1 h afforded 1,1,3-tribromoazulene-2-one (5a). 3-Bromo-1,2-azulenequinone (2a) was obtained by the hydrolysis of 5a in the presence of Ag2O. Annulated compound 6 was readily obtained by the reaction of 2a with o-phenylenediamine.