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Phenazine 5,10 dioxides N- and O-substituted were synthesized using microwave irradiation from the corresponding amino- and hydroxy-derivatives. Attempts to obtain phenazine 5,10-dioxides N- and O-substituted in conventional heating conditions, when it occurred, conducted to the desired products in extremely low yields with very long reaction times. In order to obtain phenazine 5,10-dioxide N- and O-substituted in good yields and lower reaction times, microwave irradiation was studied. In these experiments, we obtained new 2-benzyloxy, 2-benzylamino and 2-sulphonamino phenazine 5,10-dioxide derivatives successfully, in low yields, however, significantly higher than those obtained with conventional heating. Theoretical studies suggest that low nucleophilicity of 2-amino and 2-hydroxy phenazines studied is related to the presence of the moieties N,N-dioxide. DOI: 10.5935/1984-6835.20130083Fenazina 5,10 dióxidos N-e O-substituídos foram sintetizadas utilizando a irradiação de micro-ondas a partir dos correspondentes amino e hidroxi-derivados. As tentativas de N- ou O-substituição em condições de aquecimento convencionais, quando ocorreu, conduziu à formação dos produtos desejados em rendimentos extremamente baixos e em tempos de reação muito longos. A fim de obter as fenazinas 5,10-dióxidos N-ou-O-substituídas em melhores rendimentos e em menor tempo, foi estudada a reação em condições de irradiação de micro-ondas. Nestes estudos, obteve-se com êxito novos derivados 2-benziloxi, benzilamino e 2-sulfonamino phenazine 5,10-dióxidos, em baixos rendimentos, porém, significativamente maiores que aqueles obtidos através de aquecimento convencional. Estudos teóricos sugerem que a baixa nucleofilicidade das 2-amino and 2-hidroxifenazinas estudas esteja relacionada à presença da subunidade N,N-dióxido. DOI: 10.5935/1984-6835.2013008

N-andO-Reaction of 2-Amino and 2-Hydroxyphenazine 5,10-Dioxide Via Microwave Irradiation