SYNTHESIS AND PROPERTIES OF MACROHETEROCYCLIC AZOMETHINES
2777
1
3
555 w, 1588 m, 1598 m, 1626 w, 2868 m, 2922 m,
030 w, 3067 w. H NMR spectrum, δ, ppm: 3.63 br. s
Research Institute of Chemical Reagents and High-
Purity Chemical Substances under financial support by
the Ministry of Education and Science of the Russian
Federation (contract no. 14.595.21.0001, ID
RFMEFI59514X0001).
1
(
(
8H), 3.72–3.85 m (4H), 4.03–4.17 m (4H), 6.96 d.d
1H, J = 2.4, 8.5 Hz), 7.01 d (1H, J = 8.5 Hz), 7.08 d
(
1H, J = 2.4 Hz), 7.79–7.84 m (2H), 7.70–7.76 m (3H).
1
3
C NMR spectrum, δ , ppm: 68.46, 68.64, 68.76,
C
6
1
%
%
8.81, 69.73, 70.48, 106.89, 113.75, 114.73, 121.94,
42.79, 143.49, 148.13, 148.98, 150.39, 156.63. Found,
REFERENCES
1
. Biological Inorganic Chemistry. Structure and
Reactivity, Bertini, I., Gray, H.B., Stiefel, E.I., and
Valentine, J.S., Eds., Sausalito, CA: University Science
Books, 2007.
: C 64.69; H 6.57; N 7.58. C H N O . Calculated,
20 24 2 5
: C 64.50; H 6.53; N 7.52.
-[3-(5-Nitrofuran-2-yl)prop-2-en-1-ylideneamino]-
4
benzo-15-crown-5 (5) was synthesized in a similar
way from 1.41 g (0.005 mol) of 4-aminobenzo-15-
crown-5 and 0.535 mL (0.006 mol) of 3-(5-nitrofuran-
2
3
4
. Faridbod, F., Ganjali, M.R., Dinarvand, R., Norouzi, P.,
and Riahi, S., Sensors, 2008, vol. 8, p. 1645. DOI:
1
0.3390/s8031645.
2
-yl)prop-2-enal in 14 mL of methanol; the mixture
. Güler, H., Hayvalı, Z., Dal, H., and Hökelek, T.,
Polyhedron, 2012, vol. 31, p. 688. DOI: 10.1016/
j.poly.2011.10.034.
was kept for 1 h at 35°C. Yield 86%, red powder, mp
–
1
1
8
1
48.2–149.9°C. IR spectrum, ν, cm : 763 w, 809 w,
58 w, 939 w, 981 w, 1050 m, 1128 s, 1257 s, 1322 w,
352 s, 1393 w, 1468 s, 1511 s, 1560 w, 1632 s, 2871
m, 2921 m, 3040. H NMR spectrum, δ, ppm: 3.62 br.s
. Castro-Juiz, S., Fernandez, A., Lopez-Torres, M.,
Vazquez-Garcıa, D., Suarez, A.J., and Vila, J.M.,
Organometallics, 2009, vol. 28, p. 6657. DOI: 10.1021/
om900390a.
1
(
(
8H), 3.73–3.82 m (4H), 4.03–4.14 m (4H), 6.87 d.d
1H, J = 2.2, 8.5 Hz), 6.94–7.01 m (2H), 7.14 d.d (1H,
5
6
. Safin, D.A., Robeyns, K., and Garcia, Y., Cryst. Eng.
Commun., 2012, vol. 14, p. 5523. DOI: 10.1039/
C2CE25600B.
J = 8.5, 16.0 Hz), 7.21–7.30 m (2H), 7.79 d (1H, J =
3
5
5
.9 Hz), 8.51 d (1H, J = 8.5 Hz). Found, %: C 58.33; H
.76; N 6.54. C H N O . Calculated, %: C 58.35; H
2
1
24
2
8
. Hayvali, Z., Hayvali, M., and Kili, Z., J. Inclusion
Phenom. Macrocycl. Chem., 2003, vol. 45, p. 285. DOI:
.76; N 6.52
-(Biphenyl-4-ylmethylideneamino)benzo-15-
crown-5 (6) was synthesized in a similar way from
1
0.1023/A: 1024568309739.
4
7. Hayvali, Z., Hayvali, M., Kili, Z., and Hokeiek, T.,
J. Mol. Struct., 2001, vol. 597, p. 223. DOI: 10.1016/
S0022-2860(01)00603-2.
1
0
1
3
1
7
1
.41 g (0.005 mol) of 4-aminobenzo-15-crown-5 and
.95 mL (0.006 mol) of biphenyl-4-carbaldehyde in
0 mL of methanol; the mixture was kept for 1.5 h at
5°C. Yield 89%, light green powder, mp 152.3–
53.5°C. IR spectrum, ν, cm : 489 w, 567 w, 696 w,
26 w, 768 m, 799 w, 848 w, 875 w, 936 w, 982 m,
052 m, 1132 s, 1228 m, 1264 s, 1308 w, 1359 w, 1425
8
. Yam, V.W.W., Wong, K.M.C., and Lee, V.W.M.,
Organometallics, 1995, vol. 14, p. 4034. DOI: 10.1021/
om00009a002.
–
1
9
. Vae, Z.U., Lee, S.B., Chang, S.R., and Kim, U.R.,
J. Korean Chem. Soc., 2001, vol. 45, no. 1, p. 31.
w, 1453 m, 1508 s, 1540 w, 1558 w, 1584 w, 1622 s,
1
0. Zhao, L., Chen, X., Guo, F., Gou, B., and Yang, Ch.,
J. Lumin., 2014, vol. 145, p. 486. DOI: 10.1016/
j.jlumin. 2013.08.012.
1
2
869 m, 2929 m, 3045 w, 3070 w. H NMR spectrum,
δ, ppm: 3.63 br.s (8H), 3.75–3.84 m (4H), 4.04–4.16 m
4H), 6.90 d.d (1H, J = 2.3, 8.5 Hz), 6.95–7.05 m (2H),
.37–7.45 m (2H), 7.46–7.56 m (2H), 7.72–7.79 m
(
7
11. Burlov, A.S., Tsukanov, A.V., Borodkin, G.S., Revin-
skii, Yu.V., Dubonosov, A.D., Bren’, V.A., Granov-
skii, A.D., Tsivadze, A.Yu., and Minkin, V.I., Russ. J.
Gen. Chem., 2006, vol. 76, no. 6, p. 992. DOI: 10.1134/
S1070363206060259.
(
(
2H), 7.80–7.87 m (2H), 7.97–8.04 m (2H), 8.71 s
1H). Found, %: C 72.48; H 6.57; N 3.13. C H NO .
27
29
5
Calculated, %: C 72.56; H 6.60; N 3.20.
1
1
2. Klimenko, L.S. and Mart’yanov, T.P., Vestn. Yugorsk.
Gos. Univ., 2009, no. 3 (14), p. 37.
ACKNOWLEDGMENTS
3. Pedersen, C.J., J. Am. Chem. Soc., 1967, vol. 89, no. 26,
This study was performed using the facilities of the
Research Analytical Center of the State Scientific
p. 7017. DOI: 10.1021/ja01002a035.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 12 2015