SYNTHESIS AND SPECTRAL PROPERTIES OF 6(1H)-OXOPYRIDINE-2,3-DICARBOXYLIC ACID
129
4
5
13
0.02 mol of corresponding metal chloride was heated
H ), 7.26 s (1H, H ), 7.01 s (1H, NH). C NMR spec-
in a quartz tube at 200 C for 30 min, after which it
was cooled, powdered, washed with 10% ammonia,
water, reprecipitated from concentrated hydrobromic
acid, filtered off, washed with DMF, hot water, acetone,
and dried. The resulting complexes were blue powders
readily soluble in mineral acids, sparingly soluble in
DMF, DMSO, and 1-chloronaphthalene, and insoluble
in apolar organic solvents and aqueous alkalis.
trum (DMSO-d ), C, ppm: 139.05, 117.21, 104.38,
6
100.78, 98.31, 97.74, 77.36. Found, %: C 51.15; H
2.01; N 27.00. C H N NiO . Calculated, %: C
2
8
12 12
4
52.62; H 1.89; N 26.30.
ACKNOWLEDGMENTS
The work was financially supported by the Mi-
nistry of Education of the Russian Federation, Scien-
tific Research of High School in Priority Fields of
Science and Technics Program, Subprogram 203:
Chemical Technologies (project no. 203.03.02.005).
Copper(II) 1,8,15,22-tetraazaphtalocyanine-
,9,16,23(1H,8H,15H,22H)-tetraone (III), yield
2
0
.40 g (51%). Electronic absorption spectrum,
max
(
(
(
(
D), nm: in DMSO: 643 (0.396), 582 (0.156), 332
0.254); in 27% HCl: 628 (0.71), 577 (0.21), 330
0.30); and in H SO : 663 (1.31), 635 (0.83), 596
REFERENCES
2
4
1
0.46), 332 (0.82). IR spectrum, , cm : 3108 (NH),
1
2
. Boots, G., Khimiya sinteticheskih krasitelei (Che-
mistry of Synthetic Dyes), Leningrad: Khimiya, 1977,
vol. 5, p. 211.
. Phthalocyanines: Properties and Application, Les-
noff, C.C. and Lever, A.B.P., Eds., New York: VCH,
1989, vol. 1; 1993, vols. 2, 3; 1996, vol. 4.
. Akopov, A.S., Berezin, B.D., and Bykova, V.V., Teor.
Exp. Khim., 1979, vol. 15, no. 4, p. 458.
. Gal’pern, M.G. and Luk’yanets, E.A., Zh. Obshch.
Khim., 1969, vol. 39, no. 11, p. 2536.
2
7
922 (CH), 1701 (C=O), 1506, 1394 (C=N), 1138,
58, 739. Found, %: C 52.84; H 2.21; N 26.90.
C H CuN O . Calculated, %: C 52.22; H 1.88;
2
8
12
12
4
N 26.10.
Cobalt(II) 1,8,15,22-tetraazaphtalocyanine-
,9,16,23(1H,8H,15H,22H)-tetraone (IV), yield
2
3
4
5
0
.37 g (47%). Electronic absorption spectrum,
max
(
(
D), nm: in DMF: 629 (1.07), 574 (0.24), 406 sh
0.27), 329 (0.51); in DMF (anhydrous): 678 (0.201),
4
(
72 (0.234); in 27% HCl: 622 (0.79), 548 (0.23), 334
0.45); in DMSO: 627 (0.70), 571 (0.22), 334 (0.66);
and in H SO : 643 (0.45), 617 (0.37), 583 (0.26), 323
. Akopov, A.S., Surov, I.V., and Berezin, B.D., Teor.
Exp. Khim., 1984, vol. 20, no 6, p. 744.
2
4
1
6. Surov, I.V., Akopov, A.S., and Berezin, B.D., Koord.
Khim., 1986, vol. 12, no. 1, p. 72.
7. Osipov, Yu.M., Shaposhnikov, G.P., Kulinich, V.P.,
and Korzhenevskii, A.B., Izv. Vyssh. Uchebn. Zaved.
Khim. Khim. Tekhnol., 1987, vol. 30, no. 9, p. 29.
(
1
0.75). IR spectrum, , cm : 3116 (NH), 2926 (CH),
709 (C=O), 1510, 1391 (C=N), 1131, 754, 743.
+
+
Mass spectrum, m/z: 639 [M] , 872 [M + 160 + 73] ,
9
+
45 [M + 160 + 146] . Found, %: C 42.25; H 1.94;
N 19.66. C H Br C N O . Calculated, %: C
2
8
12
2
°
12
4
4
2.16; H 1.51; N 21.09.
8. Shaposhnikov, G.P., Kulinich, V.P., and Maiz-
lish, V.E., Uspekhi khimii porfirinov (Advances in
Porphyrin Chemistry), St. Petersburg: Research Inst.
Khimii, St.-Peterb. Gos. Univ., 1999, vol. 2, p. 190.
Nickel(II) 1,8,15,22-tetraazaphtalocyanine-
,9,16,23(1H,8H,15H,22H)-tetraone
2
(V),
yield
0.42 g (58%). Electronic absorption spectrum,
max
9
. Radyushkina, K.A., Merenkova, M.V., and Tarase-
vich, M.R., Elektrokhimiya, 1992, vol. 28, no. 7,
p. 1032.
(
(
(
D), nm: in DMF: 641 (1.10), 577 (0.21), 410 sh
0.30), 330 (0.52); and in 27% HCl: 645 (0.72), 578
0.24), 331 (0.37). IR spectrum, , cm : 3106 (NH),
1
2
923 (CH), 1699 (C=O), 1358 (C=N), 1085, 773, 611.
10. Bykova, V.V., Cand. Sci. (Chem.) Dissertation,
1
H NMR spectrum (DMSO-d ), , ppm: 7.52 s (1H,
Ivanovo, 1981.
6
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 1 2005