1,3-DIPOLAR CYCLOADDITION REACTIONS
587
8. Tome, A.C., Science of Synthesis, Storr, R.C. and
Gilchrist, T.L., Eds., Stuttgart: Thieme, 2004, vol. 13,
p. 415.
1,1′-[(6-Methyl-2,4-dioxo-1,2,3,4-tetrahydropy-
rimidine-1,3-diyl)bis(pentane-5,1-diyl)]bis(3-meth-
yl-4-octyl-1H-1,2,3-triazol-3-ium) bis(4-toluenesul-
fonate) (XIX). A mixture of 0.4 g (0.6 mmol) of
compound XIV and 1.2 g (6.5 mmol) of methyl
p-toluenesulfonate was stirred for 10 h on heating at
90–100°C. The mixture was cooled to room tempera-
ture, 20 ml of diethyl ether was added, and the solvent
was separated by decanting. This procedure was re-
peated five times. Yield 0.48 g (80%), oily substance.
1H NMR spectrum, δ, ppm: 0.88 m (6H, CH3), 1.26–
1.66 m (32H, 2′-H, 3′-H, 2′′′-H–7′′′-H), 2.03 m (4H,
4′-H), 2.17 s (3H, 6-CH3), 2.76 m (4H, 4″-CH2), 3.74–
3.82 m (2H, 1-CH2), 3.88 m (2H, 3-CH2), 4.18 br.s
(6H, 3″-CH3), 4.62 m and 4.68 m (2H each, 1″-CH2),
5.53 s (1H, 5-H), 8.94 s and 9.05 s (1H, 5-H). Mass
spectrum: m/z 825.5 [M – OTs]+ . Found, %: C 61.40;
H 8.03; N 11.25; S 6.49. C51H80N8O8S2. Calculated, %:
C 61.42; H 8.08; N 11.24: S 6.43. M 996.55.
9. Kitazaki, T., Ichikawa, T., Tasaka, A., Hosono, H.,
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This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 10-03-00365), by the Presidium of the Russian
Academy of Science (Program no. 8), and by the
President of the Russian Federation (program for state
support of young Russian candidates of sciences,
project no. MK-5936.2012.3).
15. Semenov, V.E., Voloshina, A.D., Toroptzova, E.M.,
Kulik, N.V., Zobov, V.V., Giniyatullin, R.Kh., Mikhai-
lov, A.S., Nikolaev, A.E., Akamsin, V.D., and Rez-
nik, V.S., Eur. J. Med. Chem., 2006, vol. 41, p. 1093.
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mov, Y.Y., Latypov, S.K., and Reznik, V.S., Eur. J. Org.
Chem., 2007, p. 4578.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 4 2012