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Reactions of 2-aryl-4-methoxy-9-oxocyclohepta[b]pyrylium perchlorates with hydroxylamine and hydrazines
Authors:Dao-Lin Wang  Kimiaki Imafuku
Abstract:2-Aryl-4-methoxy-9-oxocycloheptab]pyrylium perchlorates 1a-c reacted with hydroxylamine hydrochloride and hydrazine sulfate in the presence of triethylamine to afford 2-aryl-4,9-dihydrocycloheptab]pyran-4,9-dione 4-oximes 3a-c and 4-hydrazones 4a-c in good yields, respectively. On the other hand, the reactions with methylhydrazine and phenylhydrazine gave respectively 1-methyl- and 1-phenyl-substituted 5-aryl-3-(3-tropolonyl)pyrazoles 5a-c and 6a-c in excellent yields. Treatment with 4-nitrophenylhydrazine gave 2-aryl-4,9-dihydrocycloheptab]pyran-4,9-dione 4-(4-nitrophenyl)hydrazones 7a-c in good yields.
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