1
062
MIKHAILOV et al.
1
′
–1
spectrum (CDCl ), δ , ppm: 11.94 (CH ), 118.43 (C ),
lished data [25]: mp 266°C. IR spectrum, ν, cm : 715,
3
C
3
3
′
5′
1
24.77 (C ), 127.01 (C ), 128.97 (2C, C H ), 129.88
752, 959, 1044, 1084, 1138, 1164, 1245, 1320, 1352,
1393, 1435; 1477 (C–N); 1530, 1552 (C=C); 1573,
1606 (C=N). H NMR spectrum (DMSO-d ), δ, ppm:
2.63 s (3H, CH ), 6.51 d.d (1H, 5′-H, J = 7.5, 7.6 Hz),
6.72 d (1H, 3′-H, J = 7.6 Hz), 7.26 d.d (1H, 5′-H, J =
7.5, 7.6 Hz), 7.73 d (1H, 6′-H, J = 7.5 Hz). Mass
spectrum, m/z (I , %): 32 (15), 39 (27), 41 (33), 43
(9), 51 (18), 53 (19), 58 (14) [CH C=NOH] , 64 (31),
6
5
4
′
(
1
1
Cquat), 130.85 (2C, C H ), 131.00 (C H ), 131.10 (C ),
6
5
2′
6
5
6
′
3
1
34.11 (C ), 149.90 (C ), 165.72 (C=O), 167.85 (C ),
6
5
3
73.38 (C ). Mass spectrum, m/z (I , %): 32 (7), 39
4), 43 (5), 50 (6), 51 (18), 63 (7), 64 (5), 77 (68)
C H ] , 83 (4), 91 (6) [C H ] , 92 (8) [C H O] , 93 (9)
C H OH] , 105 (100) [C H CO] , 106 (15), 119 (5)
2-HOC H CN] , 120 (3) [2-HOC H C=NH] , 121 (2)
2-HOC H CO] , 130 (2), 139 (2), 147 (3), 152 (2),
75 (5) [M – C H CO] , 209 (5), 218 (4), 236 (3) [M –
N O] , 254 (4), 280 (15) [M] . Found, %: C 68.40; H
rel
3
3
3
(
[
[
[
[
1
+
+
+
3
6
5
7
7
6
4
+
+
6
4
6
5
rel
+
+
+
6
4
6
4
3
+
+
+
66 (17), 77 (12) [C H ] , 78 (9), 91 (29) [C H ] , 92
6
4
6 5 7 7
+
+
+
(37) [C H O] , 93 (6) [C H OH] , 94 (78), 105 (8)
6 4 6 4
6
5
+
+
+
+
[C H O] , 119 (44) [2-HOC H CN] , 120 (52)
2
7 5 6 4
+
+
4
4
.30; N 9.80. C H N O . Calculated, %: C 68.57; H
[2-HOC H C=NH] , 121 (28) [2-HOC H CO] , 143
6 4 6 4
1
6
12
2
3
+
.32; N 9.99. M 280.
(11), 155 (4), 176 (100) [LH] , 183 (31), 185 (7), 242
6
4
+
66
+
(
63) [L Zn – L] , 244 (35) [L Zn – L] , 291 (3),
2
2
2
-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl 4-methyl-
benzenesulfonate (3g). Oxadiazole 2, 0.34 g (2 mmol),
was dissolved in 10 mL of methyl ethyl ketone, 5.52 g
6
4
+
3
4
27 (5), 363 (6), 379 (4), 400 (3), 414 (22) [L Zn] ,
2
66
+
16 (12) [L Zn] . M 415.
2
(
0
8 mmol) of freshly calcined potassium carbonate and
.37 g (2 mmol) of p-toluenesulfonyl chloride were
Bis[(3-methyl-1,2,4-oxadiazol-5-yl)phenolato]-
copper(II) (4b) was synthesized as described in [25].
added, and the mixture was refluxed for 3 h and
diluted with 30 mL of ice water. The precipitate was
filtered off, washed with water (3×30 mL), dried in
air, and recrystallized from propan-2-ol. Yield 0.46 g
Yield 59%, light brown crystals, mp 230–232°C;
–
1
published data [25]: mp 228°C. IR spectrum, ν, cm :
715, 748, 772, 854, 959, 1051, 1085, 1141, 1167, 1252,
1306, 1336, 1394, 1429; 1471 (C–N); 1533, 1548
(C=C); 1572, 1607 (C=N). Mass spectrum, m/z (Irel,
(
47%), colorless crystals, mp 87–89°C. IR spectrum, ν,
–
1
cm : 699, 734, 767, 783, 802, 823, 861, 1043, 1088;
%): 32 (18), 39 (35), 40 (12), 43 (8), 50 (14), 51 (20),
+
1
1
1
171 (SO ); 1198, 1298, 1312, 1343; 1374 (SO );
52 (15), 53 (13), 58 (17) [CH C=NOH] , 63 (72), 64
2
2
3
+
448, 1467; 1495 (C–N); 1556, 1588 (C=C); 1595,
(42), 65 (32), 76 (9), 77 (8) [C H ] , 78 (10), 91 (31)
[C H ] , 92 (82) [C H O] , 93 (13) [C H OH] , 104 (17),
105 (8) [C H O] , 106 (9), 119 (64) [2-HOC H CN] ,
7 5 6 4
6
5
1
+
+
+
615 (C=N). H NMR spectrum (CDCl ), δ, ppm: 2.38
3
7 7 6 4 6 4
+
+
s (3H, CH ), 2.40 s (3H, CH C H ), 7.23 d (2H, o-H,
3
3
6
4
3
3
+
+
J = 7.5 Hz) , 7.41 d.d (1H, 5′-H, J = 7.5, 7.6 Hz), 7.45
d (1H, 3′-H, J = 7.6 Hz), 7.57 d.d (1H, 4′-H, J = 7.5,
.6 Hz), 7.65 d (2H, m-H, J = 7.5 Hz), 7.96 d (1H, 6′-
H, J = 7.5 Hz). C NMR spectrum (CDCl ), δ , ppm:
120 (83) [2-HOC H C=NH] , 121 (67) [2-HOC H CO] ,
6 4 6 4
3
3
+
129 (4), 139 (4), 141 (11), 155 (4), 176 (100) [LH] ,
181 (19), 183 (40), 185 (15), 238 (65) [L Cu – L] ,
239 (8), 240 (29) [L Cu – L] , 254 (3), 272 (2), 291
3
63
+
7
2
3
13
65
+
3
C
2
1
′
1
1.97 (CH ), 22.11 (CH C H ), 119.29 (C ), 125.10
(3), 300 (3), 327 (3), 342 (2), 363 (4), 379 (3), 400 (2),
3
3
6
4
3
′
5′
o
m
63
+
65
+
(
(
(
(
6
[
1
1
(
C ), 127.95 (C ), 129.01 and 129.98 (C , C ), 131.52
C ), 132.36 (C ), 134.05 (C ), 146.07 (C ), 147.59
C ), 167.69 (C ), 172.99 (C ). Mass spectrum, m/z
I , %): 32 (5), 39 (8), 43 (6), 50 (7), 51 (6), 63 (10),
413 (16) [L Cu] , 414 (2), 415 (7) [L Cu] . M 414.
2
2
4
′
i
6′
p
2
′
3
5
ACKNOWLEDGMENTS
rel
This study was performed under financial support
by the Ministry of Education and Science of the
Russian Federation in the framework of state assign-
ment (project no. 4.129.2014/K).
+
4 (9), 65 (25), 76 (7), 77 (8) [C H ] , 89 (5), 91 (100)
6
5
+
+
+
C H ] , 92 (18) [C H O] , 102 (4), 105 (8) [C H O] ,
7 7 6 4 7 5
+
+
19 (4) [2-HOC H CN] , 120 (4) [2-HOC H C=NH] ,
6 4 6 4
21 (3) [2-HOC H CO] , 132 (2), 139 (3), 147 (4), 155
+
6
4
+
53) [CH C H SO ] , 164 (3), 176 (8) [M + H –
3 6 4 2
REFERENCES
+
CH C H SO ] , 182 (4), 208 (5), 245 (5), 266 (48)
3
6
4
2
+
+
1
2
. Jiang, P. and Guo, Z., Coord. Chem. Rev., 2004, vol. 248,
p. 205. DOI: 10.1016/j.cct.2003.10.013.
[
M – SO ] , 330 (6) [M] . Found, %: C 58.30; H 4.30;
2
N 8.60; S 9.60. C H N O S. Calculated, %: C 58.17;
1
6
14
2
4
. Mikhailov, I.E., Kolodina, A.A., Dushenko, G.A.,
Artyushkina, Yu.M., Tkachev, V.V., Aldoshin, S.M.,
Sayapin, Yu.A., and Minkin, V.I., Chem. Heterocycl.
Compd., 2014, vol. 50, no. 6, p. 828. DOI: 10.1007/
s10593-014-1537-9.
H 4.27; N 8.48; S 9.71. M 330.
Bis[(3-methyl-1,2,4-oxadiazol-5-yl)phenolato]-
zinc(II) (4a) was synthesized as described in [25].
Yield 55%, colorless crystals, mp 267–269°C; pub-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 5 2016