KOBELEVSKAYA et al.
1508
10. Joo-Yong, Y., Sang-gi, L., and Hyunik, S., Curr. Org.
Chem., 2011, vol. 15, p. 657.
11. Bakr, F.A.W., Rizk, E.K., and Abdelbasset, A.F.,
Arkivoc, 2011, part (i), p. 196.
12. Khidre, R.E., Mohamed, H.A., and Abdel-Wahab, B.F.,
0.233 g (1 mmol) of 1-benzyl-5-chloro-3-(prop-1-en-2-
yl)-1H-pyrazole (1d) and 0.124 g (1 mmol) of thiol 2e;
reaction time 3 h. Yield 0.278 g (78%). IR spectrum, ν,
cm–1: 3134, 3086, 3062, 3029, 2957, 2928, 2870, 1602,
1513. 1H NMR spectrum, δ, ppm: 1.27 d (3H, CH3, J =
7.0 Hz), 2.51 m (1H, CH2), 2.69 m (1H, CH2), 2.93 m
(1H, CH), 3.59 s (2H, CH2), 5.33 s (2H, CH2), 5.97 s
(1H, 4-H), 7.13–7.25 m (10H, C6H5). Found, %:
C 67. 22; H 5. 96; Cl 9. 97; N 7. 83; S 9. 02.
C20H21ClN2S. Calculated, %: C 67.31; H 5.93; Cl 9.93;
N 7.85; S 8.98.
Turk. J. Chem., 2013, vol. 37, p. 1.
13. Türkoglu, G., Ulldemolins, C.P., Müller, R., Hübner, E.,
Heinemann, F.W., Wolf, M., and Burzlaff, N., Eur. J.
Inorg. Chem., 2010, p. 2962.
14. Han, L.C.M. and Timmons, R.B., Chem. Mater., 1998,
vol. 10, p. 1422.
15. Chang, S.Y., Chen, J.L., and Chi, Y., Inorg. Chem.,
1-Benzyl-3-[2-(benzylsulfanyl)propyl]-5-chloro-
1H-pyrazole (3j) was synthesized from 0.233 g
(1 mmol) of 1-benzyl-5-chloro-3-(prop-1-en-1-yl)-1H-
pyrazole (1e) and 0.090 g (1 mmol) of thiol 2e;
reaction time 3 h. Yield 0.250 g (70%). IR spectrum, ν,
cm–1: 3138, 3086, 3068, 3025, 2924, 2854, 1608, 1511.
1H NMR spectrum, δ, ppm: 1.20 d (3H, CH3, J =
6.3 Hz), 2.65 m (1H, CH), 2.85 m (2H, CH2), 3.68 s
(2H, CH2), 5.23 s (2H, CH2), 5.97 s (1H, 4-H), 7.12–
7.24 m (10H, C6H5). Found, %: C 67.18; H 5.95;
Cl 9.95; N 7.86; S 9.06. C20H21ClN2S. Calculated, %:
C 67.31; H 5.93; Cl 9.93; N 7.85; S 8.98.
2007, vol. 46, p. 11202.
16. Fokin, S., Ovcharenko, V., Romanenko, G., and Ikor-
skii, V., Inorg. Chem., 2004, vol. 43, p. 969.
17. Cavero, E., Uriel, S., Romero, P., Serrano, J.L., and
Gimenez, R., J. Am. Chem. Soc., 2007, vol. 129,
p. 11608.
18. Tebbji, K., Bouabdellah, I., Aouniti, A., Hammouti, B.,
Oudda, H., Benkaddour, M., and Ramdani, A., Mater.
Lett., 2007, vol. 61, p. 799.
19. Junges, F., Kuhn, V.C.A., dos Santos, A.H.D.P.,
Rabello, C.R.K., Thomas, C.M., Carpentier, J.-F., and
Casagrande, O.L., Organometallics, 2007, vol. 26,
p. 4010.
20. Guerrero, M., Pons, J., and Ros, J., J. Organomet.
Chem., 2010, vol. 695, p. 1957.
The main results of this study were obtained using
the facilities of the Baikal Joint Analytical Center,
Siberian Branch, Russian Academy of Sciences.
21. Lupidi, G., Marchetti, F., Masciocchi, N., Reger, D.L.,
Tabassum, S., Astolfi, P., Damiani, E., and Pettinari, C.,
J. Inorg. Biochem., 2010, vol. 104, p. 820.
REFERENCES
1. Fustero, S., Sanchez-Rosello, M., Barrio, P., and Simon-
Fuentes, A., Chem. Rev., 2011, vol. 111, p. 6984.
2. Janin, Y.L., Chem. Rev., 2012, vol. 112, p. 3924.
22. Potapov, S., Nudnova, E.A., Domnina, G.A., Kirpo-
tina, L.N., Quinn, M.T., Khlebnikov, A.I., and Schepet-
kin, I.A., Dalton Trans., 2009, p. 4488.
23. Bouwman, E., Driessen, W.L., and Reeddijk, J., Coord.
Chem. Rev., 1990, vol. 104, p. 143.
24. Es’kova, L.A., Erushnikova, L.A., Afonin, A.V., and
Domnina, E.S., Russ. Chem. Bull., 1992, vol. 41,
p. 1462.
3. Elguero, J., Goya, P., Jagerovic, N., and Silva, A.M.S.,
Targets in Heterocyclic Systems. Chemistry and
Properties, Attanasi, O.A. and Spinelli, D., Rome: Ital.
Soc. Chem., 2003, vol. 6, p. 53.
4. Pérez-Fernández, R., Goya, P., and Elguero, J., Arkivoc,
2014, part (ii), p. 233.
25. Maksimova, M.A., Cand. Sci. (Chem.) Dissertation,
Irkutsk, 2007.
5. Schmidt, A. and Dreger, A., Curr. Org. Chem., 2011,
vol. 15, p. 1423.
6. Schmidt, A. and Dreger, A., Curr. Org. Chem., 2011,
26. Levkovskaya, G.G., Kobelevskaya, V.A., Rudyako-
va, E.V., Ha, Q.K., Samultsev, D.O., and Rozen-
tsveig, I.B., Tetrahedron, 2011, vol. 67, p. 1844.
vol. 15, p. 2897.
27. Levkovskaya, G.G., Rudyakova, E.V., Kobelev-
skaya, V.A., Popov, A.V., and Rozentsveig, I.B.,
Arkivoc, 2016, part (iii), p. 82.
28. Rudyakova, E.V., Samultsev, D.O., Levanova, E.P., and
Levkovskaya, G.G., Russ. J. Org. Chem., 2013, vol. 49,
p. 734.
7. Pizzuti, L., Barschak, A.G., Stefanello, F.M.,
Farias, M.D., Lencina, C., Roesch-Ely, M., Cunico, W.,
Moura, S., and Pereira, C.M.P., Curr. Org. Chem., 2014,
vol. 18, p. 115.
8. Ivachtchenko, A.V., Russ. Chem. Rev., 2014, vol. 83,
p. 439.
9. Gouda, M.A., Abu-Hashem, A.A., Saad, H.H., and
Elattar, K.M., Res. Chem. Intermed., 2016, vol. 42,
p. 2119.
29. Rudyakova, E.V., Samultsev, D.O., and Levkov-
skaya, G.G., Russ. J. Org. Chem., 2012, vol. 48,
p. 1388.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 54 No. 10 2018