POTKIN et al.
554
ν, cm–1: 3302 (N–H); 1760 (C=O); 1632, 1589, 1567,
1510 (C=C, C=N). H NMR spectrum, δ, ppm: 2.39 s
Cl 27.43; N 10.59. C16H12Cl3N3O2. Calculated, %:
C 49.96; H 3.14; Cl 27.65; N 10.93. M 384.62.
1
(3H, Me), 2.50 s (3H, Me), 5.83 br.s (2H, NH2), 6.98 s
5-(4,5-Dichloro-1,2-thiazol-3-yl)-3-[5-(2,5-di-
methylphenyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazole
(IX). Yield 91%, mp 177–179°C. IR spectrum, ν, cm–1:
1593, 1587, 1573, 1545, 1488 (C=C, C=N). H NMR
spectrum, δ, ppm: 2.41 s (3H, Me), 2.54 s (3H, Me),
3
(1H, 4-H), 7.20 d (1H, Harom, J = 8 Hz), 7.23 d (1H,
3
13
H
arom, J = 8 Hz), 7.57 s (1H, Harom). C NMR spec-
trum, δC, ppm: 21.03 (Me), 21.23 (Me), 100.60 (C4),
129.07 (CHarom), 131.50 (CHarom), 131.58 (CHarom),
125.69, 126.02, 133.51, 136.10, 150.10, 151.10, 153.48,
155.61, 156.06, 171.76 (C=O). Mass spectrum:
m/z 392 (35Cl) [M – H2O]+. Found, %: C 46.52; H 3.17;
Cl 17.56; N 13.88; S 8.07. C16H12Cl2N4O3S. Calculat-
ed, %: C 46.73; H 2.94; Cl 17.24; N 13.63; S 7.80.
M 411.26.
1
2.74 s (3H, Me), 6.95 s (1H, 4-H), 7.23 d (1H, Harom
,
3
3J = 8 Hz), 7.24 d (1H, Harom, J = 8 Hz), 7.63 s (1H,
H
arom). 13C NMR spectrum, δC, ppm: 21.04 (Me), 21.21
(Me), 101.89 (CH), 129.18 (CHarom), 131.62 (2CHarom),
125.61, 125.94, 133.50, 136.20, 148.75, 151.93,
152.43, 162.37, 169.37, 172.16. Mass spectrum:
m/z 392 (35Cl) [M]+. Found, %: C 48.98; H 2.77;
Cl 18.27; N 14.57; S 8.25. C16H10Cl2N4O2S. Calculat-
ed, %: C 48.87; H 2.56; Cl 18.03; N 14.25; S 8.15.
M 393.24.
3-[5-(2,5-Dimethylphenyl)-1,2-oxazol-3-yl]-
5-methyl-1,2,4-oxadiazole (VII). A solution of 1.37 g
(5 mmol) of compound IV in 20 ml of glacial acetic
acid was heated for 6 h under reflux. The mixture was
then poured into 200 ml of water and neutralized to
pH ~7 with a solution of potassium hydroxide. The
precipitate was filtered off, washed with water, dried
under reduced pressure, and recrystallized from etha-
nol. Yield 1.23 g (96%), mp 93–95°C. IR spectrum, ν,
This study was performed under financial support
by the Byelorussian Republican Foundation for Basic
Research (project no. Kh07-050).
REFERENCES
1
cm–1: 1589, 1580, 1567, 1507 (C=C, C=N). H NMR
1. Yamamoto, T., Fujita, K., Asari, S., Chiba, A., Kataba, Y.,
Ohsumi, K., Ohmuta, N., Iida, Y., Ijichi, C., Iwayama, S.,
Fukuchi, N., and Shoji, M., Bioorg. Med. Chem. Lett.,
2007, vol. 17, p. 3736.
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khe, M.M., and Trivedi, G.K., Tetrahedron Lett., 2008,
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hauer, H., Heinecke, K., Bernoster, K., Dost, R., and
Rundfeldt, C., Eur. J. Med. Chem., 2007, vol. 42, p. 873.
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spectrum, δ, ppm: 2.40 s (3H, Me), 2.52 s (3H, Me),
2.74 s (3H, Me), 6.95 s (1H, 4-H), 7.20 d (1H, Harom
,
3
3J = 8 Hz), 7.22 d (1H, Harom, J = 8 Hz), 7.63 s (1H,
H
arom). 13C NMR spectrum, δC, ppm: 21.56 (Me), 21.03
(Me), 21.18 (Me), 101.48 (C4), 129.15 (CHarom),
131.50 (CHarom), 131.57 (CHarom), 126.05, 133.41,
136.15, 152.86, 161.76, 171.81, 177.91. Mass spec-
trum: m/z 255 [M]+. Found, %: C 65.73; H 5.35;
N 16.34. C14H13N3O2. Calculated, %: C 65.87; H 5.13;
N 16.46. M 255.27.
Compounds VIII and IX were synthesized in
a similar way.
5. Petkevich, S.K., Potkin, V.I., and Kaberdin, R.V., Russ. J.
Org. Chem., 2004, vol. 40, p. 1146.
6. Zil’berman, E.N., Reaktsii nitrilov (Reactions of Nitriles),
3-[5-(2,5-Dimethylphenyl)-1,2-oxazol-3-yl]-
5-(2,3,3-trichloroprop-2-en-1-yl)-1,2,4-oxadiazole
(VIII). Yield 94%, mp 89–91°C. IR spectrum, ν, cm–1:
Moscow: Khimiya, 1972, p. 104.
1
1607, 1581, 1552, 1505 (C=C, C=N). H NMR spec-
7. Chesnyuk, A.A., Mikhailichenko, S.N., Konyushkin, L.D.,
Firgang, S.I., and Zaplishnyi, V.N., Izv. Ross. Akad. Nauk,
2005, no. 8, p. 1845.
8. Takhistov, V.V., Prakticheskaya mass-spektrometriya
organicheskikh soedinenii (Practical Mass Spectrometry
of Organic Compounds), Leningrad: Leningr. Gos. Univ.,
1977, p. 265.
trum, δ, ppm: 2.40 s (3H, Me), 2.52 s (3H, Me), 4.37 s
3
(2H, CH2), 6.97 s (1H, 4-H), 7.22 d (1H, Harom, J =
8 Hz), 7.23 d (1H, Harom, 3J = 8 Hz), 7.63 s (1H, Harom).
13C NMR spectrum, δC, ppm: 21.03 (Me), 21.19 (Me),
34.27 (Me), 101.57 (C4), 129.17 (CHarom), 131.60
(2CHarom), 123.22, 123.59, 125.96, 133.47, 136.18,
152.53, 162.10, 172.05, 175.08. Mass spectrum:
m/z 383 (35Cl) [M]+. Found, %: C 49.68; H 3.44;
9. Takhistov, V.V., Rodin, A.A., and Maksimova, B.N., Usp.
Khim., 1991, vol. 60, p. 2143.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 4 2009