978
M. A.Saleh, Y. A. Hafez, F. E. Abdel-hay, W. I. Gad
Vol. 40
(s, 1H, CH-pyrazole ring), 6.59-7.13 (m, 5H, Ph), 7.63 (t, 1H, H-
8, J = 8.2 Hz), 7.79 (t, 1H, H-6, J = 8.2 Hz), 7.92 (t, 1H, H-7, J =
for 6 hours. After cooling the precipitate was collected, washed
with ethanol, dried and recrystallized from ethanol to give com-
pound 17. Yield 2.8 g (70%); mp 280-282 °C; ir (KBr): 3378
(NH), 3049 (C-H aromatic), 1731 (CO), 1693 (CO), 1605, 1518
8.2 Hz), 8.17 (d, 1H, H-5, J = 8.2 Hz), 8.97 (s, 1H, exchangeable
+
with D O, NH); ms: m/z (ion, relative intensity): 331 (M ,
2
+
+
-1 1
27.08), 316(M -Me, 1.48), 301(316-Me, 2.73), 239 (M -NHPh,
15.25), 145 (239-C H N , 15.62), 119 (144-CN, 20.10), 104
(C=N, C=C) cm ; H nmr (DMSO-d ): δ 6.92-8.02 (m, 13H,
6 H
Ar-H), 9.30 (s, 1H, exchangeable with D O, NH), 10.35 (s, 1H,
5
6
2
2
13
(119-NH, 3.14), 76 (104-CO, 100).
Anal. Calcd. for C N O (331.4): C, 68.87; H, 5.17; N,
exchangeable with D O, NH of hydrazino);
C nmr (DMSO-
2
H
d ): δ 150.6, 166.0, 124.2, 127.0, 127.4, 136.0, 121.6 and 148.1
19 17
5
6 C
21.13. Found: C, 69.10; H, 5.00; N, 21.43.
(C-2, C-4, C-4a, C-5, C-6, C-7, C-8 and C-8a (quinazolinone car-
bon atoms, respectively), 136.0, 114.4, 129.6 and 118.6 (phenyl
carbon atoms due to ipso, ortho, meta and para, respectively),
160.6, 147.2, 126.0, 129.6, 121.6, 130.0, 114.4, 135.5 (C-1, C-3,
C-3a, C-4, C-5, C-6, C-7 and C-7a (isoindole carbon atoms,
respectively).
3-[(4-Oxo-3-phenylamino-3,4-dihydroquinazolin-2-yl)hydra-
zono]butyric Acid Ethyl Ester (15).
A mixture of hydrazino compound 12 (2.67 g, 0.01 mole) and
ethyl acetoacetate (3.0 ml, 0.023 mole) was refluxed in methanol
(20 ml) for 3 hours. The reaction mixture was cooled and the sol-
vent was evaporated to dryness. The residue was recrystallized
from benzene/petroleum ether to give compound 15 as yellow
crystals. Yield 1.90 g (50%); mp 79-80 °C; ir (KBr): 3425 (NH),
1726 (CO ester), 1687 (CO quinazolinone), 1623 , 1548 (C=N,
Anal. Calcd. for C
H N O (397.4): C, 66.49; H, 3.80; N,
22 15 5 3
17.62. Found: C, 66.90; H, 3.60; N, 18.00.
REFERENCES AND NOTES
-1
1
C=C) cm ; H nmr (DMSO-d ): δ 1.23 (s, 3H, CH ), 1.98 (t,
6
H
3
*
Corresponding author. E-mail: MAHSALEH@hotmail.com
3H, CH of ester, J = 7.0 Hz), 3.40 (s, 2H, CH ), 3.82 (q, 2H,
3
2
[1] F. K. Kirchnov and A. W. Zalay, US Patent, 3, 217,005
(1965); Chem. Abstr., 64, 3570 (1966).
CH , J = 7.0 Hz), 6.10-7.97 (m, 9H, Ar-H), 8.20 (s, 1H,
2
exchangeable with D O, NH), 10.25 (s, 1H, exchangeable with
[2] K. Kar, J. Chatterjee and B. Mukherji, J. Sci & Ind. Research,
85, 159 (1960); Chem. Abstr., 55, 6704 (1961).
[3] V. Z. Gorkin and R. S. Krivchenkova, Vop Med. Khim, 14, 428
(1967); Chem. Abstr., 67, 87675 (1967).
[4] I. Ahmad, J. Indian Chem. Soc., 65, 362 (1988).
[5] G. H. F. Nuttal, Proc. Camb. Phil. Soc., 15, 53 (1909); Chem.
Abstr., 3, 1301 (1909).
[6] I. A. Mazur, R. S. Kalkewick and P. N. Steplywle, Farmzho, 4,
34 (1980); Chem. Abstr., 94, 47258 (1981).
[7] G. Tanaka, Japan Kokai, 7495, 973 (1974); Chem. Abstr., 82,
156320 (1975).
2
13
D O, NH); C nmr (DMSO-d ): δ 14.5 (CH ), 17.2 (CH ),
2
6
C
3
3
37.2 (CH ), 60.0 (CH ), 113.5, 120.0, 120.3, 122.2, 122.2, 128.0,
2
2
129.1, 129.1, 135.6, 136.5, 148.0 (C
) 158.2 (-N=C-), 160.1
arom
(C=O quinazolinone), 169.4 (C=O butyric ethyl ester); ms: m/z
+
+
(ion, relative intensity): 379 (M , 63.97), 364 (M -Me, 7.35),
334 (364-CH O, 7.35), 292 (334-C H O, 100), 236 (292-
2
2 2
C H N , 25.75), 145 (33.08), 119(19.55), 104 (7.00), 77 (33.08).
2
3 2
Anal. Calcd. for C
H N O (379.4): C, 63.31; H, 5.58; N,
20 21 5 3
18.46. Found: C, 63.60; H, 5.60; N, 18.73.
[8] K. Spirkova, S. Stankovsky and J. Homacek, Collect. Czech.
Chem. Commun., 59, 243 (1994).
[9] A. A. Bekhit and M. A. Khalil, Pharmazie, 53, 539 (1998).
[10] A. M. E. Omar, H. M. Salama and N. H. Eshba, Farmaco Ed.
Sci., 40, 49 (1985).
[11] M.. Rajopadhye and F. D. Popp, J. Heterocyclic Chem., 24,
1637 (1987).
[12] T. Szirtes, L. Kisfaludy, E. Palosi and L. Szporny, J. Med.
Chem., 29, 1654 (1986).
[13] K. Mogilaiah and R. B. Rao, Indian J. Chem., Sec.B, 37, 894
(1998).
[14] G. Coppi, A. Falcone and S. Manzardo, Arzneim Forsch, 44,
12a, 1417 (1994).
[15] R. Lesyke, O. Vladzimirska, B. Zimenkovsky, M. Horishny
and I. Nektegayev, Boll. Chem. Farm., 137, 210 (1998).
[16] N. S. Habib, S. Fahmy, S. M. El- Khawass and T. A. Aziem,
Pharmazie, 55 (12), 900 (2000).
2-[N’-(2-Oxo-2-dihydroindol-3-ylidene)-hydrazino-3-pheny-
lamino-3H-quinazolin-4-one (16).
A mixture of hydrazino compound 12 (2.67, 0.01 mol) and
isatin (1.47 g, 0.01 mol) in ethanol (50 ml) in the presence of 2
drops of glacial acetic acid as catalyst was refluxed for 4 hours.
During this period, the product was separated from the reaction
mixture as yellow precipitate. The precipitate was collected by fil-
tration and recrystallized from butanol to give compound 16.
Yield 3.2 g (80%); mp 276 °C; ir (KBr): 3427(NH), 2922 (C-H
aromatic), 1708 (CO), 1668 (CO), 1618, 1546 , 1462 (C=N, C=C)
-1
1
cm ; H nmr (DMSO-d ): δ 6.62-8.20 (m, 13H, Ar-H), 8.79 (s,
6
H
1H, exchangeable with D O, NH), 10.53 (s, 1H, exchangeable
2
with D O, NH of hydrazino), 11.43 (s, 1H, exchangeable with
2
13
D O, NH of isatin); C nmr (DMSO-d ): δ 154.1, 165.6, 123.1,
2
6
C
127.9, 127.4, 135.4, 117.4 and 145.7 (C-2, C-4, C-4a, C-5, C-6, C-
7, C-8 and C-8a (quinazolinone carbon atoms, respectively),
142.7, 109.5, 128.8 and 112.2 (phenyl carbon atoms due to ipso,
ortho, meta and para, respectively), 159.7, 146.8, 119.3, 128.8,
121.2, 131.0, 114.4 and 138.8 (C-2, C-3, C-3a, C-4, C-5, C-6, C-7
and C-7a (isatin carbon atoms, respectively).
[17] M. F. Abdel-Megeed, G. A. El-Hiti, M. A. Abdo and M.
A.Saleh , Revue Roumaine De Chimie, 45, 545 (2000).
[18] M. A. Saleh, Y. A. Abbas, F. E. Abdel-Hai and S. A. Youssef,
Nucleosides, Nucleotides & Nucleic Acids, 20, 1891 (2001).
[19] M. A. Saleh, M. F. Abdel-Megeed, M. A. Abdo and A. M.
Shokr, Nucleosides, Nucleotides & Nucleic Acids, 21, 93 (2002).
[20] M. A. Saleh, M. F. Abdel-Megeed, M. A. Abdo and A. M.
Shokr, J. Heterocyclic Chem., 40, 85 (2003).
[21] M. A. Saleh, M. F. Abdel-Megeed, M. A. Abdo and A. M.
Shokr, Molecules, 8, 363 (2003).
[22] M. A. Saleh and M. F. Abdel-Megeed, J. Carbohydr. Chem.,
22, 79 (2003).
Anal. Calcd. for C
H N O (396.4): C, 66.66; H, 4.07; N,
22 16 6 2
21.20. Found: C, 66.68; H, 4.10; N, 21.29.
2-(4-Oxo-3-phenylamino-3,4-dihydroquinazolin-2-ylamino)-
isoindole-1,3-dione (17).
πA mixture of hydrazino compound 12 (2.67 g, 0.01 mole) and
phthalic anhydride (1.48 g, 0.01 mole) in methanol (50 ml) in the
presence of 2 drops of glacial acetic acid as catalyst was refluxed
[23] H. K Gakhar, S. C. Gupta and N. Kumar, Indian J. Chem.,
Sec.B, 20, 14 (1981).
[24] R. Umarani, Magn. Reson. Chem., 30, 1027 (1992).