1
668
GOLOVANOV et al.
1
yellow needles, mp 192.5-193.5°С (Me CO–H O). Н
ACKNOWLEDGMENTS
2
2
NMR spectrum (400 MHz, DMSO-d ), δ, ppm: 3.33–3.37
m (2Н, Н ), 3.84 s (3Н, МеО), 3.99–4.03 m (2Н, Н ),
6
4
5
This work was financially supported by a grant
from the Ministry of Education and Science of the
Russian Federation, Resolution no. 220, contract no.
14.B25.31.0011.
6
7
.90 t (1Нarom, J 7.32 Hz), 7.09 d (2Нarom, J 8.6 Hz),
.15 d (2Нarom, J 7.9 Hz), 7.23 s (1Н, Нisox), 7.29–7.35
1
3
m (2Нarom), 7.87 (2Нarom, J 8.5 Hz). С NMR spectrum
4
5
(100 MHz, DMSO-d ), δ, ppm: 31.9 (C H ), 48.7 (C H ),
6 2 2
REFERENCES
4
5
1
5.9 (МеО), 100.9 (C ); 113.7, 115.1, 120.4, 121.3,
isox
5
1. Abass, M., Abdel-Megid, M., and Hassan, M., Synth.
28.7, 129.6, 138.8 (Сarom); 144.9 (Cisox), 161.4, 162.4
3
3
isox
Commun., 2013, vol. 43, p. 329.
2. Karthikeyan, K., Seelan, T.V., Lalitha, K.G., and Peru-
(
C
), 164.6 (C ). Mass spectrum, m/z (I , %):
pyrazole
rel
+
3
19 (100) [M] , 275 (5.1), 187 (4.4), 171 (27.8), 159
mal, P.T., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 3370.
(
(
3
3
11.0), 146 (50.4), 131 (5.1), 119 (6.5), 104 (17.7), 91
3
. An, H., Kim, H.-J., Jung, N.-J., Jang, H., Park, J.-W.,
and Suh, Y.-G., Bioorg. Med. Chem. Lett., 2011, vol. 21,
p. 6297.
8.2), 77 (31.8), 64 (6.5), 51 (5.9). Found, m/z
+
20.1394 [M + H] . С H N O . Calculated, M + H
1
9
17
3
2
20.1394.
4
. Carrión, M.D., Camacho, M.E., León, J., Escames, G.,
Tapias, V., Acuna-Castroviejo, D., Gallo, M.A., and
Espinosa, A., Tetrahedron, 2004, vol. 60, p. 4051.
5
-(1-Phenyl-4,5-dihydro-1H-pyrazol-3-yl)-3-(4-
chlorophenyl)-1,2-oxazole (3d). Yield is 95%.
1
5. Spiteri, C., Keeling, S., and Moses, J.E., Org. Lett.,
010, vol. 12, p. 3368.
. Golovanov, A.A. and Odin, I.S., Russ. J. Org. Chem.,
015, vol. 51, p. 447. doi 10.1134/S1070428015030306
Yellow needles, mp 205°C (Me CO–H O). Н NMR
2
2
2
spectrum (400 MHz, DMSO-d ), δ, ppm: 3.34–3.38 m
6
6
7
4
5
(
2Н, Н ), 4.00–4.05 m (2Н, Н ), 6.91 t (1Нarom, J 7.2 Hz),
2
7
7
.15 d (2Нarom, J 7.9 Hz), 7.30–7.36 m (3Нarom + Н ),
.60 d (2Нarom, J 8.2 Hz), 7.96 d (2Нarom, J 8.6 Hz). С
isox
. Golovanov, A.A., Odin, I.S., Bekin, V.V., Vologzhani-
na, A.V., Bushmarinov, I.S., Zlotskii, S.S., Gerasi-
mov, Yu.L., and Purygin, P.P., Russ. J. Org. Chem.,
2016, vol. 52, p. 414. doi 10.1134/S1070428016030209
1
3
NMR spectrum (100 MHz, DMSO-d ), δ, ppm: 31.9
6
4
5
4
(
1
1
C H ), 48.8 (C H ), 100.9 (C ); 113.8, 120.5, 127.8,
29.0, 129.6, 129.7, 135.6, 138.6 (Сarom); 144.8 (Cisox),
), 165.1 (Cisox). Mass spectrum, m/z (Irel,
): 323 (100) [M] , 184 (5.7), 171 (36.6), 150 (30.3),
2 2 isox
5
8. Malacria, M. and Roumestant, M.L., Tetrahedron, 1977,
vol. 33, p. 2813.
3
3
61.9 (C
pyrazole
+
%
9. Bondarev, G.N., Ryzhov, V.A., Chistokletov, V.N., and
Petrov, A.A., Zh. Org. Khim., 1967, vol. 3, p. 821.
0. Reimlinger, H. and Vandewalle, J.J.M., Lieb. Ann.,
1
23 (11.1), 104 (26.9), 91 (15.0), 77 (44.1), 64 (6.3), 51
+
1
1
(
11.1). Found, m/z 324.0898 [M + H] . С H ClN O.
18 14 3
1
968, vol. 720, p. 117. doi 10.1002/jlac.19687200110
Calculated, M + H 324.0898.
1. Nightingale, D. and Wadsworth, F., J. Am. Chem. Soc.,
3
-(3-Nitrophenyl)-5-(1-phenyl-4,5-dihydro-1H-
1945, vol. 67, p. 416.
pyrazol-3-yl)-1,2-oxazole (3e). Yield 95%, Yellow
12. Miller, R.D. and Reiser, O., J. Heterocycl. Chem., 1993,
1
needles, mp 205-206°C (Me CO–H O). Н NMR
vol. 30, p. 775.
2
2
1
3. Botvinnik, E.V., Blandov, A.N., and Kuznetsov, M.A.,
Russ. J. Org. Chem., 2001, vol. 37, p. 421. doi 10.1023/
A:1012448911890
spectrum (400 МHz, DMSO-d ), δ, ppm: 3.35–3.40
6
4
5
m (2Н, Н ), 4.02–4.06 m (2Н, Н ), 6.91 t (1Нarom, J
7
7
8
.3 Hz), 7.16 d (2Нarom, J 7.9 Hz), 7.33 t (2Нarom, J
.9 Hz), 7.53 s (1Н, Нisox), 7.85 t (1Нarom, J 8.1 Hz),
.34–8.41 m (2Нarom) 8.70 s (1Harom). С NMR
1
1
1
4. Braude, E.A., Linstead, R.P., and Wooldridge, K.R.,
J. Chem. Soc., 1956, p. 3070.
5. Liu, K.-C., Shelton, B.R., and Howe, R.K., J. Org.
Chem., 1980, vol. 45, p. 3916.
6. Sheldrick, G.M., SADABS v. 2.01, Bruker/Siemens Area
Detector Absorption Correction Program, Madison,
Wisconsin, USA: Bruker AXS, 1998.
1
3
spectrum (100 МHz, DMSO-d ), δ, ppm: 31.8
6
4
5
4
(
C H ), 48.8 (C H ), 101.1 (Cisox); 113.8, 120.6,
2 2
1
21.7, 125.3, 129.6, 130.5, 131.4, 133.4, 138.4
5
3
(
(
[
(
(
С
C
); 144.7 (Cisox), 149.0, 161.3 (Cpyrazole), 165.6
). Mass spectrum, m/z (I , %): 334 (100)
rel
arom
3
isox
+
1
1
7. Sheldrick, G.M., Acta Cryst., 2015, vol. А71, p. 3.
8. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J.,
Howard, J.A.K., and Puschmann, H., J. Appl. Cryst.,
2009, vol. 42, p. 339.
M] , 304 (7.2), 288 (10.0), 189 (17.2), 171 (25.4), 157
7.0), 143 (22.4), 130 (6.2), 115 (13.5), 104 (35.5), 91
18.5), 77 (61.5), 64 (9.2), 51 (11.5). Found, m/z
+
3
3
35.1139 [M + H] . С H N O . Calculated, M + H
19. Brandsma, L., Preparative Acetylenic Chemistry,
1
8
14
4
3
35.1139.
Amsterdam–Oxford–New York–Tokyo: Elsevier, 1988.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 11 2017