678
F. A. ATTABY ET AL.
2-[(3-Amino-4-phenyl-6-pyridin-3-ylthieno[2,3-b]pyridin-2-yl)carbonyl]-5-meth
yl-2,4-dihydro-3H-pyrazol-3-one (24a) as yellow crystals (86%), mp = >330◦C; IR (ν
cm−1): 3386 (NH2), 3148 (NH), 3058 (aromatic-CH), 1681 (CO); MS: 427 (M+, 15.3%
corresponding to the molecular formula C23H17N5O2S of the assigned structure), 386 (M+
COCH, 24.0%), 385 (M+ CH3CNH, 92.9%); Anal., Calcd./Found(%): C(64.62/64.66)
H(4.01/4.05) N(16.38/16.40) S(7.50/7.54).
2-[(3-Amino-4-methoxyphenyl-6-pyridin-3-ylthieno[2,3-b]pyridin-2-yl)-carbon
yl]-5-methyl-2,4-dihydro-3H-pyrazol-3-one (24b) as yellow crystals (70%), mp =
>330◦C; IR (ν cm−1): 3422, 3363 (NH2), 3068 (aromatic-CH), 1682, 1662 (two CO);
MS: 441 (M+ NH2 54.2%), 440 (M+ NH2, H,), 439 (M+ NH2, 2H, 100%); Anal.,
Calcd./Found(%): C(63.01/63.06) H(4.19/4.22) N(15.31/15.35) S(7.01/7.07).
Synthesis of 26a,b
A solution of 3a,b (0.20 g, 0.21 g, 0.00055 mol) and diethyl malonate (0.09 g,
0.00055 mol) in acetic acid (15 mL) was heated under reflux for 5 h. The excess solvent
was evaporated and cooled. The solid was collected by filtration, dried, and crystallized
from the acetic acid to give 24a,b, respectively.
1-{[3-Amino-4-(4-phenyl)-6-pyridin-3-ylthieno[2,3-b]pyridin-2-yl]carbonyl}
pyrazolidine-3,5-dione (26a) as pale yellow crystals (77%), mp = 280◦C; IR (ν cm−1):
3262, 3203 (NH2), 3052 (aromatic-CH), 1673, 1634 (two CO); MS: 428 (M+ H, 5.1%),
427 (M+ 2H, 12.6%), 314 (M+ NH2, NCOCH2CONH, 10.0%); 1H NMR (DMSO-D6)
(δ ppm): 2.50 (s, 2H, CH2); 6.01 (s, 2H, NH2); 7.49–9.40 (m, 11H, Phenyl, pyridinyl
Hꢀs and NH); Anal., Calcd./Found(%): C(61.53/61.56) H(3.52/3.55) N(16.31/16.35)
S(7.47/7.52).
1-{[3-Amino-4-(4-methoxyphenyl)-6-pyridin-3-ylthieno[2,3-b]pyridin-2-yl]car-
bonyl}pyrazolidine-3,5-dione (26b) as yellow crystals (67%), mp = 300–302◦C; IR
(ν cm−1): 3485, 3362 (NH2), 3246 (NH), 2958 (aromatic-CH), 1716, 1671. (two CO);
MS: 458 (M+ H, 21.7%), 457 (M+ 2H, 43%), 415 (M+ H, CONH, 85.7%), 360
(M+ NCOCH2CONH, 100%), 332 (M+ CONCOCH2CONH, 9.2%), 316 (M+ NH2,
CONCOCH2CONH, 15.0%); Anal., Calcd./Found(%): C(60.12/60/.16) H(3.73/3.78)
N(15.24/15.27) S(6.98/7.01).
REFERENCES
1. A. M. Hussin, F. A. Abu-Shanab, and E. A. Ishak, Phosphorus, Sulfur, and Silicon, 159, 55
(2000).
2. F. A. Attaby and A. M. Abdel-Fattah, Phosphorus, Sulfur, and Silicon, 155, 253 (1999).
3. A. E. Abdel-Rahman, E. A. Bakhite, and E. A. Al-Taifi, J. Chin. Chem. Soc., 49, 223 (2002).
4. G. P. Moloney, Molecules, 6, M203 (2001).
5. S. Furuga, N. Choh, N. Suzuki, and T. Imada, PCT Int. Appl. WO 00000493(2002); Chem.
Abstr., 132, 64179s (2000).
6. A. Krauze, S. Germame, O. Eberlins, I. Sturms, V. Klusa, and G. Duburs, Eur. J. Med. Chem.,
34, 301 (1999).
7. J. M. Quintela, C. Peinador, C. Veiga, L. Gonzales, L. M. Botana, A. Alfonso, and R. Riguera,
Bioorg. Med. Chem., 6, 1911 (1998).
8. J. M. Quintela, C. Peinador, L. Gonzales, R. Iglesias, A. Parama, F. Alvares, M. L. Sanmartin,
and R. Riguera, Eur. J. Med. Chem., 38, 265 (2003).