Summary.
Several pyrazino[2,3-b]phenazine derivatives were prepared by the reaction of 2,3-diaminophenazine with different 1,2-diketones. Nucleophilic substitution of 2,3-dibromomethyl-pyrazino[2,3-b]phenazine with propanol, morpholine, and potassium thiocyanate gave 2,3-bis-(propoxymethyl)-pyrazino[2,3-b]phenazine, 2,3-bis-(4-morpholinylmethyl)-pyrazino[2,3-b]phenazine, and 2,3-bis-(cyanosulfanylmethyl)-pyrazino[2,3-b]phenazine. 2-Aryl-1H-imidazo[4,5-b]phenazine derivatives were synthesized by a one-pot reaction of 2,3-diaminophenazine with different aromatic aldehydes or acids. Reaction of 2,3-diaminophenazine with acetic anhydride and formic acid afforded 1H-imidazo[4,5-b]phenazine and 2-methyl-1H-imidazo[4,5-b]phenazine. Chemical and spectroscopic evidences for the product structures of the new compounds are presented.
Zusammenfassung.
Einige Pyrazino[2,3-b]phenazinderivate wurden durch Reaktion von 2,3-Diaminophenazin mit verschiedenen 1,2-Diketonen dargestellt. Nucleophile Substitution von 2,3-Dibrommethyl-pyrazino[2,3-b]phenazin mit Propanol, Morpholin und Kaliumthiocyanat ergab 2,3-Bis(propoxymethyl)-pyrazino[2,3-b]phenazin, 2,3-Bis-(4-morpholinylmethyl)-pyrazino[2,3-b]phenazin und 2,3-Bis-(cyanosulfanylmethyl)-pyrazino[2,3-b]phenazin. 2-Aryl-1H-imidazo[4,5-b]phenazinderivate wurden in einer Eintopfreaktion aus 2,3-Diaminophenazin mit verschiedenen aromatischen Aldehyden oder Carbonsäuren hergestellt. Reaktion von 2,3-Diaminophenazin mit Essigsäureanhydrid oder Ameisensäure lieferte 1H-Imidazo[4,5-b]phenazin und 2-Methyl-1H-imidazo[4,5-b]phenazin. Chemische und spektroskopische Nachweise für die Struktruren der neuen Verbindungen werden mitgeteilt.
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Received December 29, 1998. Accepted February 2, 1999
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Amer, A., El-Bahnasawi, A., Mahran, M. et al. On the Synthesis of Pyrazino[2,3-b]phenazine and 1H-Imidazo[4,5-b]phenazine Derivatives. Monatshefte fuer Chemie 130, 1217–1225 (1999). https://doi.org/10.1007/PL00010183
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DOI: https://doi.org/10.1007/PL00010183