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Azaindoles are heterocyclic aromatic organic compounds. Azaindoles have bicyclic structure, consisting of pyrrole ring fused to a pyridine ring. The azaindole moiety exhibits excellent potential for biological activity, while structurally differing from indole only by additional ring nitrogen. Azaindole can be classified into different forms such as 4-azaindole, 5-azaindole, 6-azaindole and 7-azaindole. The properties of 7-azaindoles are governed by the two N-heteroatomic rings with opposite pi-electron effects. The 7-azaindoles are stronger bases than indoles with pKa of 4.59 for azaindole, and influenced by the two heteroaromatic rings with opposite electron properties.
A few naturally occurring azaindole-containing compounds have been isolated. Most azaindoles have been prepared traditionally by classical methods such as Fischer, Madelung and Reissert procedures. 7-Azaindoles have been extensively investigated for uses in biological probes and imaging. Being isosteres of indoles, they have been the target of extensive synthetic efforts to explore their potent pharmacological activities. They also have applications in material synthesis. 7-azaindoles are excellent blue emitters for organic LEDs (light emitting diodes). With a wide range of metal ions, they readily form coordination complexes, and their metal complexes display not only phosphorescence but also unusual and often unprecedented reactivity toward C-H and C-X bonds (Review: Luminescence and reactivity of 7-azaindole derivatives and complexes, Zhao, SB. et al., Chem. Soc Rev., 2010, 39(8), 142-56).