928
GAVRISHOVA et al.
4-Phenyl-2,6-bis(4-azidophenyl)pyridine (IIIa)
tained by the three-stage synthesis from commercially
available compounds.
and 2,4,6-tris(4-azidophenyl)pyridine (IIIb). Water,
4 ml, then concentrated hydrochloric acid, 2 ml, were
added to 0.50 mmol of corresponding bis- or trisami-
nophenylpyridine. The resulting solution was cooled to
0°С and diazotized by a NaNO2 solution (1.00 mmol for
bis-aminophenylpyridine and 1.50 mmol for trisami-
nophenylpyridine) in 3 ml of H2O. Within 30 min the
solution was cooled to 1°С, and 0.5 ml of concentrated
hydrochloric acid and 1 ml of water were added to it with
stirring. Then a solution of 1.00 or 1.50 mmol of NaN3
in 3 ml of H2O was added and, within a few minutes of
that, an excess amount of an azide. The precipitate was
filtered off and twice recrystallized from petroleum ether.
White crystals of a corresponding azide were obtained
(darken in the course of time).
This work was financially supported by the Russian
Foundation for Basic Research (project no. 03-03-32116).
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CDCl3, TMS), δ, ppm (J, Hz): 8.21 (4H, d, J = 8.7,
C6H4), 7.84 (2Н, s, pyridine), 7.73 (2Н, d, J = 8.5, C6H5),
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decomposition (from petroleum ether). IR spectrum, ν
(cm–1): 2127, 1296 (N3). 1H NMR spectrum (400 MHz,
CDCl3, TMS), δ, ppm (J, Hz): 8.19 (4H, d, J = 8.9,
C6H4), 7.78 (2Н, s, pyridine), 7.72 (2Н, d, J = 8.7, C6H4),
7.12–7.24 (6H, m, C6H4). Found (%): C 64.36, H 3.47,
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CONCLUSION
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New di- and triazidophenylpyridines have been ob-
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 83 No. 5 2010