3,4-Benzotropolone and Related Compounds. VIII. Azo, Nitro and Amino Derivatives of 6-Hydroxy-2,3-benzotropone
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概要
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On diazo coupling and nitration, 6-hydroxy-2,3-benzotropone (I) and its 5-bromo derivative (II) gave their 7-azo (V and VI) and 7-nitro substitution products (VII and VIII), respectively. In the same reactions, 7-bromo-6-hydroxy- (III) and 5,7-dibromo-6-hydroxy-2,3-benzotropones (IV) replaced their 7-bromo substituent to give the same 7-azo and 7-nitro substitution products as above. On nitration of III and IV, 2,2-dibromo- (IX) and 2,2,7-tribromo-4,5-benzocyclohepta-4,6-diene-1,3-diones (X) were also formed. Hydrogenation of V, VI, VII and VIII gave 7-amino-6-hydroxy-2,3-benzotropone (XI), diazotization of which gave 2-diazo-4,5-benzocyclohepta-4,6-diene-1,3-dione (XII). 7-Chloro-6-hydroxy-2,3-benzotropone (XV) was brominated to 2-bromo-2-chloro-4,5-benzocyclohepta-4,6-diene-1,3-dione (XVII) at room temperature, to 5-bromo-7-chloro-2,3-benzotropone (XVI) at 100°C, and to 2-chloro-2,7-dibromo-4,5-benzocyclohepta-4,6-diene-1,3-dione (XVIII) with excess bromine at 100°C. XVII and XVIII were easily debrominated to XV and XVI, respectively, on heating with hydrochloric or hydrobromic acid. XV changed into a mixture of I and II on heating with hydrobromic acid.
- 公益社団法人 日本化学会の論文
著者
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Ebine Seiji
Department of Chemistry, Faculty of Science and Engineering, Saitama University
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Hoshino Masamatsu
Department of Chemistry, Faculty of Science and Engineering, Saitama University
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