Synthesis and Physical Properties of Pyrido[1′,2′:1,2]imidazo[4,5-b]quinoxalines

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  • Synthesis and Physical Properties of Pyrido(1,2: 1,2)imidazo(4,5-b)quinoxalines.
  • Synthesis and Physical Properties of Py
  • Synthesis and Physical Properties of Pyrido[1′,2′ : 1,2]imidazo[4,5-<i>b</i>]quinoxalines

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A series of 2-, 3-, or 4-substituted pyrido[1′,2′ : 1,2]imidazo[4,5-b]quinoxalines (PIQs) were synthesized in moderate-to-good yields by the reactions of 2-amino-3-chloroquinoxalines (ACQs) with substituted pyridines, and the structures were established. The reactions of ACQs with 3-phenoxycarbonyl and 3-benzoylpyridines gave the corresponding 2-substituted PIQs, while those with 3-methyl, 3-ethyl, 3-benzyl, 3-phenyl, 3-ethoxycarbonyl, and 3-acetylpyridines gave the corresponding 4-substituted PIQs. PIQ derivatives having substituents at the 2,4,8, and/or 9-positions were also studied. The spectroscopic and electrochemical properties of a series of PIQs derivatives were studied. PIQ showed a strong green fluorescence at 481.5 and 505 nm (Φ = 0.40) in ethanol. The introduction of substituents at the 3 position of PIQ altered the color of the fluorescence from blue to green without deteriorating the high quantum yield of PIQ. All of the derivatives showed strong (blue to orange) fluorescence in both solution and the solid state.

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