Advances in the Chemistry of Azaindoles

Yakhontov, L. N.; Прокопов, А. А.

doi:10.1070/rc1980v049n05abeh002469

Cited by 54 publications

(19 citation statements)

References 8 publications

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“…In addition, the highest reactivity towards electrophilic substitution occurs in indole and 6-azaindole. From the series for q 3 it is evident that 5-azaindole is less inclined towards electrophilic substitution at position 3 as had been shown experimentally [2]. It should be noted here that the bond order P 23 changes in parallel with the value of the charge on atom C (2) (q 2 ).…”

mentioning

confidence: 64%

Correlations of the physicochemical parameters of azaindoles with their reactions

Kereselidze

Pachuliya

Zarkuya

et al. 2006

Chem Heterocycl Compd

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Using the AM1 semiempirical quantum method the enthalpies of formation, ionization energies, electron affinities, energy differences between highest occupied and lowest unoccupied orbitals, atomic charges, bond orders, and dipole moments have been calculated for 4-, 5-, 6-, and 7-azaindoles. A correlation has been built up between the calculated physicochemical parameters and the Hammett para-substituent and inductive constants. The 1H to 7H proton transfer in 7-azaindole has been quantitatively described.

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mentioning

confidence: 64%

Correlations of the physicochemical parameters of azaindoles with their reactions

Kereselidze

Pachuliya

Zarkuya

et al. 2006

Chem Heterocycl Compd

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“…1 H ‐Pyrrolo[2,3‐ b ]pyridine (7‐azaindole), a fused heterocyclic molecular framework, has been drawing much attention in biochemical and physicochemical studies, due to its characteristic condensed ring system. It consists of fused pyridine and pyrrole ring system and having opposite π‐electron densities.…”

Section: Introductionmentioning

confidence: 99%

Pyrrolo[2,3‐b]pyridine Derivatives: Synthesis and Preliminary Evaluation of their Calf Thymus DNA Binding Properties

2016

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Benzothiazole, benzimidazole and imidazopyridine promoted substitutions at C3 position of 1H‐pyrrolo[2,3‐b]pyridine have been reported. A new series of acylation as well as monoalkylation and dialkylation of 1H‐pyrrolo[2,3‐b]pyridine with different acyl and alkyl halides has been synthesized in moderate to good yields. Palladium catalyzed Suzuki‐Miyaura cross‐coupling has also been approached for the arylation at C6 position of imidazopyridine. Further, interaction studies of these compounds have been performed with calf thymus‐DNA using UV‐visible and fluorescence spectroscopic techniques. The effect of ionic strength and iodide, determined by absorption and emission spectra, supported the binding of compounds with ct‐DNA.

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“…8 The biological and synthetic aspects of 7-azaindole and its derivatives have been covered by previous review articles. 4,[9][10][11] 7-azaindole and its derivatives have been found to display unusual and often unique bonding modes with metal ions, leading to the formation of mononuclear and polynuclear metal complexes. In addition to stabilize species with multiple metal-metal bonds, 7-azaindole-based ligands have also been reported to promote magnetic exchange between paramagnetic metal centers.…”

Section: Introdutionmentioning

confidence: 99%

Luminescence and reactivity of 7-azaindole derivatives and complexes

Zhao

Wang

2010

Chem. Soc. Rev.

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7-Azaindole and its derivatives have been extensively investigated for uses in biological probes and imaging. In contrast, there have been very limited studies on the coordination chemistry and the applications of 7-azaindole and derivatives in materials science and in chemical bond activation. Our recent research has shown that 7-azaindolyl and derivatives are excellent blue emitters for organic light emitting diodes, they have rich coordination chemistry with both main group elements and transition metal ions, and their metal complexes display not only phosphorescence but also unusual and often unprecedented reactivity toward C-H and C-X bonds. This critical review discusses recent advances in these fields with focuses on new 7-azaindolyl derivatives and their metal complexes developed by our group. The luminescent properties and applications of 7-azaindolyl-based compounds will be presented. The reactivity of Pt(II) complexes toward C-H and C-X bonds, especially the steric impact of the bis(7-azaindolyl) chelate ligands and bimetallic cooperativity will be discussed (86 references).

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Advances in the Chemistry of Azaindoles

Cited by 54 publications

References 8 publications

Correlations of the physicochemical parameters of azaindoles with their reactions

Correlations of the physicochemical parameters of azaindoles with their reactions

Pyrrolo[2,3‐b]pyridine Derivatives: Synthesis and Preliminary Evaluation of their Calf Thymus DNA Binding Properties

Luminescence and reactivity of 7-azaindole derivatives and complexes

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