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Communication | Regular issue | Vol 29, No. 8, 1989, pp.1459-1464
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5034
Polyannulated Tropylium Compounds Having Benzothiazine and Related Heterocyclic Rings. Formation of o- and p-Benzoquinonoid Products by Rearrangement

Tetsuo Nozoe,* Kimio Shindo,* Hidetsugu Wakabayashi, and Sumio Ishikawa

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

Abstract

Tropylium compounds having tri-annulated heterocycles (11 and 15) are obtained by the reaction of 2,4-dibromo-7-methoxy- and 3,5,7-tribromo-2-methoxytropone with O-aminophenol and O-aminobenzenethiol, via di-annulated compounds. Rearrangements to di- and tri-annulated o- and p-benzoquinonoid compounds (13, 16 and 20) take place during the attempted synthesis of some tri-annulated tropylium systems. Possible pathways for these reactions are discussed.