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Communication | Regular issue | Vol 29, No. 6, 1989, pp.1005-1012
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4900
Reactions of 5-Bromo-2-methoxytropone and 8-Bromo- and 6,8-Dibromocyclohepta[b][1,4]benzoxazines with o-Aminophenol

Tetsuo Nozoe,* Hidetsugu Wakabayashi,* and Sumio Ishikawa

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

Abstract

Reaction of the title tropone (3) and 8-bromo compound (19) with o-aminophenol (4) in acetic acid affords the HBr salt of 8-(o-hydroxyanilino)cyclohepta[b][1,4]benzoxazine (21) as the main product, whereas under basic conditions treatment of 19 with 4 results in the formation of mainly 2- and 3-formylphenoxazine. Reaction of 6,8-dibromo compound 20 with 4 produces various tropylium compounds having two annulated heterocycles. Possible reaction pathways involving unusual intramolecular transpositions of heterocycles are discussed.