298 El-Sharief et al.
The mass spectrum of VIIb exhibited a molecu-
lar ion peak at 228 (100%; which is the base peak).
(0.01 mol), and triethylamine (0.5 ml) in absolute
ethanol (20 ml) was refluxed for 10 h. The solid that
was obtained was recrystallized from the proper sol-
vent to give XII (Table 1).
Preparation of Quinazolines (IXa–f)
The IR spectrum of XII exhibited the following
1
1
bonds:
at 1690 cm , and
at 3250 cm ,
at 2900 cm ,
A mixture of each substituted cyanothioformamide
(0.01 mol), anthranilic acid derivative (0.01 mol),
and triethylamine (0.5 ml) in absolute ethanol
(20 ml) was refluxed for 2 h. After evaporation of the
solvent, the obtained solid was recrystallized from a
proper solvent to give IXa–f (Table 1).
NH
CH aliph
C
O
1
1
at 1500 and 1290 cm .
C
S
The 1H NMR of compound XII (CDCl3) exhibited
the following signals: 1.8 and 2.4 (8H, cyclohexene),
7.9–8.5 (5H, m, Ar-H), 11.4 (1H, s, NH; cancelled with
D2O), 11.8 (1H, s, CSNH; cancelled with D2O). Mass
spectrum of XII assigned a molecular ion peak at
m/z 341 (95%) (Scheme 7).
1
The IR spectrum of IXb showed NH at 3170 cm
1
and
at 1699 cm . The mass spectrum of IXa
C
O
showed a molecular ion peak at m/z 192 (9.3%).
These products (IXa–f) were found to be iden-
tical with those prepared according to the literature
methods : IXa,b [17], IXc [18], IXd,e [19], and IXf
[18].
REFERENCES
[1] Walter, W.; Bode, K. D. Leibigs Ann Chem 1966, 131,
698.
[2] Papadopoulos, E. P. J Org Chem 1979, 44, 3858.
[3] Ketcham, R.; Schaumann, E. J Org Chem 1980, 45,
3748.
Preparation of Quinazolines (XIa–i)
[4] Ketcham, R. Synthesis 1980, 11, 869.
[5] Khattak, I.; Ketcham, R.; Schaumann, E.; Adiwidjaja,
G. J Org Chem 1985, 50(19), 3432.
[6] Huang, J.; Graves, M. D. J Heterocyclic Chem 1987,
24, 1781.
[7] Ammar, Y. A.; Ismail, I. M.; El-Sharief, A. M. Sh.;
Mohamed, Y. A.; Amer, R. A. J Prakt Chem 1988,
330(3), 421–427.
[8] Ammar, Y. A.; El-Sharief, A. M. Sh.; Zahran, M. A.;
El-Said, M. Z.; El-Said, U. H. J Chem Res, Synop
1995, 325.
A mixture of IV (X NH, 0.01 mol), the anthranilic
acid derivative (0.01 mol), and triethylamine (0.5 ml)
in absolute ethanol (30 ml) was refluxed for 12 h.
The solid that was obtained was recrystallized from
ethanol to give XIa–i (Table 1).
IR Spectrum of Compound XI
Compound No.
NH
C
O
C
S
[9] El-Sharief, A. M. Sh.; Ketcham, R.; Schaumann, E.;
Phosphorus, Sulfur and Silicon 1989, 46, 83–86.
[10] Mohamed, A. M.; El-Sharief, A. M. Sh.; Ammar,
Y. A.; Aly, M. M. Pharmazie 1989, 44(11), 765–
767.
[11] Mohamed, Y. A.; Ammar, Y. A.; El-Sharief, A. M.
Sh.; Aly, M. M. J Chin Chem Soc 1990, 37, 511–
516.
XIa
XIb
XIc
XId
XIe
XIf
3225
3225
3225
3240
3255
3245
1676
1686
1697
1678
1680
1693
1472–1261
1462–1236
1491–1245
1475–1260
1483–1229
1468–1229
[12] El-Sharief, A. M. Sh.; Ammar, Y. A.; Mohamed, Y. A.;
Aly, M. M.; El- Gaby, M. S. A.; Aly, A. S. Phosphorus,
Sulfur and Silicon Relat Elem 2001, 1–20.
[13] El-Sharief, A. M. Sh.; Ammar, Y. A.; Mohamed, Y. A.;
El-Gaby, M. S. A. Phosphorus, Sulfur and Silicon Re-
lat Elem 1999, 148, 117–130.
[14] El-Sharief, A. M. Sh.; Ammar, Y. A.; Mohamed, Y. A.;
El-Gaby, M. S. A. Phosphorus, Sulfur and Silicon Re-
lat Elem 1999, 148, 215–226.
[15] Saegusa, Y.; Nakamura, S. J Heterocyclic Chem 1988,
25, 1337.
[16] Farbenind, G.; A. G. Fr. (1934), 773, 944; Chem Abstr
1935, 29, 2177.
The 1H NMR spectrum of compound XIa
(CDCl3): 6.6–8.8 (9H, m, Ar-H), 11.4 (1H, s, NH; can-
celled with D2O), 12.2 (1H, s, CSNH; cancelled with
D2O). Also, 1H NMR of compound XIf (CDCl3): 7–8.8
(8H, m, Ar-H), 11.41 (1H, s, NH; cancelled with D2O),
12.23 (1H, s, CSNH; cancelled with D2O).
The mass spectrum of XIa exhibited a molar ion
peak at m/z 281 (79%), together with a base peak
at m/z 280 [(M+ 1), 100%; Scheme 5]. Also, mass
spectrum of compound XIh exhibited a molecular
ion peak at m/z 299 (95.8%), together with a base
peak at m/z 298 [(M+ 1), 100%; Scheme 6].
[17] Capuane, L.; Zander, M. Chem Ber 99(10), 1966,
3085; Chem Abstr 1967, 66, 10899z.
[18] Bharagava, B. N.; Chaursia, M. R. J Med Chem 1968,
11, 404.
[19] Bharagava, B. N.; Lakhan, R. Cur Sci 1967, 36, 575;
Chem Abstr 1968, 68, 105150f.
[20] El-Sharief, A. M. Sh.; Atalla, A. A.; Hussein, A. M.;
El-Gaby, M. S. A.; Hassan, A. A. Phosphorus, Sulfur
and Silicon Relat Elem 2000(160), 141–158.
2-Thiocarbanilide-5,6,7,8-tetrahydrobenzo[b]
thieno[2,3-d]pyrimidin-4(3H)one (XII)
A mixture of IV (X NH; 0.01 mol), 2-amino-4,5,
6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid