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KIM et al.
(2 mmol), was added to a solution of 0.640 g (1 mmol)
of triiodide 2 in 3 mL of acetone. The mixture was kept
for 24 h in a refrigerator, and the beige precipitate was
filtered off and washed with acetone (3×2 mL). Yield
CONFLICT OF INTEREST
No conflict of interest was declared by the authors.
REFERENCES
1
0.328 g (84%), mp 113–115°C (decomp.). H NMR
spectrum (DMSO-d6), δ, ppm: 3.85–3.68 m (2H,
CH2I), 4.64 d.d (1H, NCH, J = 12.7, 7.5 Hz), 5.08 d.d
(1H, NCH, J = 12.6, 9.7 Hz), 5.59–5.51 m (1H, 2-H),
7.61 t (1H, 8-H, J = 6.5 Hz), 7.71 d (1H, 6-H, J =
8.8 Hz), 8.47 t (1H, 7-H, J = 8.7 Hz), 8.71 d (1H, 5-H,
J = 6.3 Hz).
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Reaction of 2-bromomethyl-2,3-dihydro[1,3]oxa-
zolo[3,2-a]pyridinium bromide (5) with sodium
iodide. Sodium iodide dihydrate, 0.38 g (0.002 mol),
was added to a mixture of 0.29 g (0.001 mol) of
bromide 5 [20] and 3 mL of propan-2-ol, and the
mixture was refluxed for 3 h. The mixture was cooled
and filtered, and the precipitate was treated with 5 mL
of acetone and filtered off. A fivefold amount of
diethyl ether (by volume) was added to the filtrate, and
the precipitate of triiodide 2 was filtered off and dried.
Yield 0.51 g (78%), mp 124–125°C (decomp.). The
solvent was distilled off from the filtrate, the residue
was dissolved in methylene chloride, and GC/MS
analysis of the solution showed the presence of 1-
allylpyridin-2(1H)-one.
Reaction of triiodide 2 with triethylamine in
methanol. A mixture of 0.643 g (0.001 mol) of tri-
iodide 2, 5 mL of methanol, and 0.152 mL (0.001 mol)
of triethylamine was refluxed for 20 h. The mixture
was filtered, the solvent was distilled off from the
filtrate, the residue was treated with methylene
chloride, the precipitate was filtered off, and the filtrate
was evaporated. The residue was 0.314 g (86%) of
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1
1-allylpyridin-2(1H)-one. H NMR spectrum (DMSO-
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d6), δ, ppm: 4.51 d.t (2H, NCH2, J = 5.5, 1.9 Hz), 5.12
m (2H, =CH2), 5.92 m (1H, CH=), 6.15 t.d (1H, 5-H,
J = 6.6, 0.9 Hz), 6.36 d (1H, 3-H, J = 9.1 Hz), 7.48 m
(1H, 4-H), 7.58 d.d (1H, 6-H, J = 6.8, 1.0 Hz).
ACKNOWLEDGMENTS
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This study was performed under financial support
by the government of the Russian Federation
(Resolution no. 211, March 16, 2013; contract
no. 02.A03.21.0011) and by the Ministry of Education
and Science of the Russian Federation in the
framework of state assignment no. 4.9665.2017/8.9.
15. Bradsher, C. and Zinn, M.F., J. Heterocycl. Chem.,
1964, vol. 1, p. 219. doi 10.1002/jhet.5570010421
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 12 2018