An efficient and effective route to 7-azaindole framework has been produced by one-pot, three-component cyclocondensation of N-substituted 2-amino-4-cyanopyrroles, many aldehydes, and active methylene composites in ethanol or acetic acid at reflux.
Reactions involving tetronic acid, indane-1,3-dione, dimedone, and 5-phenylcyclohexane-1,3-dione gave carbocyclic fused 7-azaindole, whereas Meldrum’s acid, benzoylacetonitrile, and malononitrile occurred in the highly substituted 7-azaindole derivatives, doing this strategy very useful in diversity-oriented synthesis.
Melting point: 105-107 °C(lit.)
Boiling point: 270 °C (753.1004 mmHg)
Density 1 .1151 (rough estimate)
refractive index 1.5500 (estimate)
Flash point: 270°C
storage temp. Refrigerator
color White to off-white
CAS DataBase Reference 271-63-6(CAS DataBase Reference)
Related Categories Azaindoles, Chemical Synthesis, Building Blocks, C7 to C9,
Heterocyclic Building Blocks,
A heterocyclic molecule that can be used as a pharmaceutical building block.
Starting material in a new synthesis of azaserotonin.
1, 5 g in a glass bottle
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Imidazolinone derivatives as CGRP receptor antagonists utilized in the treatment.
Recrystallize it repeatedly from EtOH, then sublime it in a vacuum [Tokumura et al. J Am Chem Soc 109 1346 1987]. The N-acetate has m 65-66o (from *C6H6), and the pirate has m 232-233o (from Me2CO) [Clemo & Swan J Chem Soc 603 1945, Beilstein 23 III/IV 1105.]
Azaindoles are heterocyclic aromatic organic composites. Azaindoles have bicyclic composition, consisting of pyrrole ring fused to a pyridine ring. The azaindole moiety exhibits great potential for biological activity, while structurally changing from indole only by extra ring nitrogen. Azaindole can be divided into different forms such as 4-azaindole, 6-azaindole, 5-azaindole, and 7-azaindole.
The two N-heteroatomic rings direct the properties of 7-azaindoles with opposite pi-electron results. The 7-azaindoles are active bases than indoles with pKa of 4.59 for azaindole and formed by the two heteroaromatic rings with different electron properties.
A few usually occurring azaindole-containing compounds have been isolated. Most azaindoles have been made traditionally by classical methods such as Fischer, Madelung and Reissert procedures. 7-Azaindoles have been widely studied for uses in biological examinations and imaging. Being isosteres of indoles, they have been the target of great synthetic efforts to investigate their potent pharmacological activities. They also have importance in material synthesis.
7-azaindoles are great blue emitters for organic LEDs (light emitting diodes). With a broad range of metal ions, they readily form coordination complexes, and their metal complexes present not only phosphorescence but also unusual and often unprecedented reactivity to 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). Some of the leading manufacturers from Hyderabad are offering 7-Azaindole as well as 2-Amino-6-methylpyridine alkali chemicals.