R. V. Sheorey, A. Thangathiruppathy, and V. Alagarsamy
Vol 000
7
.87–7.88 (m, 2H, Ar-H), 8.51 (br s, 1H, NH D O Exchangeable);
one (6) (0.004 mol) and benzaldehyde (0.004 mol) in glacial
acetic acid was refluxed for 31 h. The reaction mixture was
poured into ice water. The solid obtained was recrystallized
2
+
MS (m/z): 218 (M ); Anal. Calcd for C H N O: C, 60.60%; H,
11 14 4
6.47%; N, 25.70%. Found: C, 60.63%; H, 6.49%; N, 25.78%.
ꢂ
ꢀ1
2
-(1-methylpropylidene-hydrazino)-3-propyl--3H-quinazolin-
from ethanol. Yield = 73%, mp 251–252 C; IR (KBr) cm
:
1
4-one (SR1). A mixture of 2-hydrazino-3-propyl-3H-quinazolin-
3360 (NH), 1693 (C = O), 1608 (C = N); H-NMR (CDCl
3
):
4
-one (6) (0.004mol) and ethyl methyl ketone (0.004mol) in
d 1.21–1.34 (t, 3H, CH CH CH ), 1.42–1.49 (m, 2H,
2 2 3
glacial acetic acid was refluxed for 34 h. The reaction mixture
CH CH CH ), 2.34–2.87 (t, 2H, CH CH CH ), 6.00 (s, 1H,
2 2 3 2 2 3
was poured into ice water. The solid obtained was recrystallized
CH), 7.32–7.34 (m, 2H, Ar-H), 7.36 (s, 1H, Ar-H), 7.43
(d, J = 2.5 Hz, 1H, Ar-H), 7.54 (s, 1H, Ar-H), 7.62 (d,
ꢂ
ꢀ1
from ethanol. Yield = 78%, mp 213–14 C; IR (KBr) cm : 3340
1
(
NH), 1670 (C = O), 1619 (C = N); H-NMR (CDCl ): d 0.98–1.04
J = 8.0 Hz, 2H, Ar-H), 8.23 (d, J = 8.0 Hz, 2H, Ar-H), 9.01
3
+
(
t, 3H, CH CH CH ), 1.23–1.24 (m, 2H, CH CH ), 1.61–69 (t,
(br s, 1H, NH, D O Exchangeable); MS (m/z): 306 (M );
2
2
3
2
3
2
2
H, CH
2
CH
2
CH
3
), 1.70–1.72 (t, 3H, CH
2
CH
3
), 2.48 (s, 3H, CH
3
),
18 4
Anal. Calcd for C18H N O: C, 70.56%; H, 5.92%, N,
2
.81–2.96 (m, 2H, CH
2
CH CH ), 7.31 (s, 1H, Ar-H), 7.44 (d,
2
3
18.28%. Found: C, 70.51%; H, 5.95%; N, 18.37%.
J = 7.5 Hz, 1H, Ar-H), 7.46–7.48 (m, 2H, Ar-H), 10.86 (br s, 1H,
2-(N-(4-chloro-benzylidene-hydrazino)-3-propyl-3H-quinazolin-
4-one (SR6). A mixture of 2-hydrazino-3-propyl-3H-quinazolin-
4-one (6) (0.004 mol) and 4-chlorobenzaldehyde (0.004 mol) in
glacial acetic acid was refluxed for 33 h. The reaction mixture was
poured into ice water. The solid obtained was recrystallized from
+
NH, D O Exchangeable); MS (m/z): 272 (M ); Anal. Calcd for
2
C H N O: C, 66.15%; H, 7.40%; N, 20.57%. Found: C, 66.11%;
15 20 4
H, 7.43%; N, 20.64%.
-(1-ethyl propylidene-hydrazino)-3-propyl-3H-quinazolin-
-one (SR2). mixture of 2-hydrazino-3-propyl-3H-
2
ꢂ
ꢀ1
4
A
ethanol. Yield = 79% yield, mp 223–224 C; IR (KBr) cm : 3260
1
quinazolin-4-one (6) (0.004 mol) and diethyl ketone (0.004 mol)
in glacial acetic acid was refluxed for 34 h. The reaction mixture
was poured into ice water. The solid obtained was recrystallized
(NH), 1682 (C = O), 1610 (C = N); H-NMR (CDCl ): d 1.11–1.21
3
(t, 3H, CH CH CH ), 1.61–1.70 (m, 2H, CH CH CH ), 2.51-
2
2
3
2
2
3
2.64 (t, 2H, CH
2
2 3
CH CH ), 6.01 (s, 1H, CH), 7.34 (s, 1H, Ar-
ꢂ
ꢀ1
from ethanol. Yield = 74%, mp 228–229 C; IR (KBr) cm
:
H), 7.38 (s, 1H, Ar-H), 7.44 (d, J = 2.5 Hz, 1H, Ar-H), 7.54 (s,
1H, Ar-H), 7.67 (d, J = 8.0 Hz, 2H, Ar-H), 8.01 (d, J = 8.0 Hz,
1
3
1
1
2
311 (NH), 1680 (C = O), 1608 (C = N); H-NMR (CDCl
3
): d
.04–1.10 (t, 3H, CH CH CH ), 1.15–1.21 (t, 2H, CH CH CH ),
2H, Ar-H), 9.21 (br s, 1H, NH, D O Exchangeable); MS (m/z):
2
2
3
2
2
3
2
+
.37–1.43 (m, 6H, (CH CH ) ), 1.78–1.90 (m, 4H, (CH CH ) ),
341 (M ); Anal. Calcd for C H N OCl: C, 63.43%; H,
2
3 2
2
3
2
18 17 4
.83–2.90 (m, 2H, CH
2
CH
2
CH
3
), 7.48 (s, 1H, Ar-H), 7.51 (d,
5.02%; N, 16.43%. Found: C, 63.40%; H, 5.06%; N, 16.35%.
2-(N-(4-nitro-benzylidene-hydrazino))-3-propyl-3H-quinazolin-
4-one (SR7). A mixture of 2-hydrazino-3-propyl-3H-quinazolin-
4-one (6) (0.004 mol) and 4-nitrobenzaldehyde (0.004 mol) in
glacial acetic acid was refluxed for 34 h. The reaction mixture
was poured into ice water. The solid obtained was
J = 7.5Hz, 1H, Ar-H), 7.62 (s, 1H, Ar-H), 7.68 (d, J = 8.0 Hz, 1H,
Ar-H), 9.03 (br s, 1H, NH, D O Exchangeable); MS (m/z): 286
2
+
(
M ); Anal. Calcd for C H N O: C, 67.10%; H, 7.74%; N,
1
6 22 4
1
9.56%. Found: C, 67.13%; H, 7.72%; N, 19.51%.
-(cyclohexylidene-hydrazino)-3-propyl-3H-quinazolin-4-one
SR3). A mixture of 2-hydrazino-3-propyl-3H-quinazolin-4-
2
ꢂ
(
recrystallized from ethanol. Yield = 78%, mp 252–254 C; IR
ꢀ
1
1
one (6) (0.004 mol) and cyclohexanone (0.004 mol) in glacial
acetic acid was refluxed for 31 h. The reaction mixture was
poured into ice water. The solid obtained was recrystallized
(KBr) cm : 3221 (NH), 1690 (C = O), 1608 (C = N); H-NMR
(CDCl ): d 1.08-1.16 (t, 3H, CH CH CH ), 1.63–1.71 (m, 2H,
3
2
2
3
CH
2
2 3 2 2 3
CH CH ), 2.62-2.64 (t, 2H, CH CH CH ), 6.03 (s, 1H,
ꢂ
ꢀ1
from ethanol. Yield = 78%, mp 230–231 C; IR (KBr) cm
:
CH), 7.24 (s, 1H, Ar-H), 7.32 (s, 1H, Ar-H), 7.47 (d,
J = 2.5 Hz, 1H, Ar-H), 7.57 (s, 1H, Ar-H), 7.69 (d, J = 8.0 Hz,
1
3
250 (NH), 1685 (C = O), 1610 (C = N); H-NMR (CDCl
3
): d
1
.10–1.22 (t, 3H, CH CH CH ), 1.29–1.86 (m, 10H, CH
2H, Ar-H), 8.05 (d, J = 8.0 Hz, 2H, Ar-H), 8.83 (br s, 1H, NH,
D O Exchangeable); MS (m/z): 351 (M ); Anal. Calcd for
2
2
2
3
2
+
cyclohexyl), 1.93–2.07 (t, 2H, CH CH CH ), 2.41–2.49 (m, 2H,
2
2
3
CH CH
2 2
3
CH ), 7.38 (s, 1H, Ar-H), 7.48 (d, J = 7.5 Hz, 1H,
18 17 5 3
C H N O : C, 61.53%; H, 4.87%; N, 19.93%. Found: C,
Ar-H), 7.52 (s, 1H, Ar-H), 7.99 (d, J = 8.0 Hz, 1H, Ar-H), 9.32
61.56%; H, 4.84%; N, 19.90%.
+
(
2
br s, 1H, NH, D O Exchangeable); MS (m/z): 298 (M ); Anal.
2-(N-(4-methoxy-benzylidene-hydrazino))-3-propyl-3H-quinazolin-
4-one (SR8). A mixture of 2-hydrazino-3-propyl-3H-quinazolin-
4-one (6) (0.004 mol) and 4-methoxybenzaldehyde (0.004 mol)
in glacial acetic acid was refluxed for 32 h. The reaction
mixture was poured into ice water. The solid obtained was
Calcd for C H N O: C, 68.43%; H, 7.43%; N, 18.77%.
17 22 4
Found: C, 68.49%; H, 7.47%; N, 18.74%.
-(N-1-phenylethylidene-hydrazino)-3-propyl-3H-quinazolin-
-one (SR4). mixture of 2-hydrazino-3-propyl-3H-
2
4
A
ꢂ
quinazolin-4-one (6) (0.004 mol) and acetophenone (0.004 mol)
in glacial acetic acid was refluxed for 30 h. The reaction
mixture was poured into ice water. The solid obtained was
recrystallized from ethanol. Yield = 74%, mp 235–236 C; IR
ꢀ
1
1
(KBr) cm : 3319 (NH), 1684 (C = O), 1602 (C = N); H-NMR
(CDCl ): d 1.06-1.16 (t, 3H, CH CH CH ), 1.51–1.62 (m, 2H,
CH CH CH ), 2.10–2.23 (t, 2H, CH CH CH ), 3.12 (s, 3H,
OCH ), 6.10 (s, 1H, CH), 7.54 (s, 1H, Ar-H), 7.56 (s, 1H, Ar-H),
3
2
2
3
ꢂ
recrystallized from ethanol. Yield = 74%, mp 223–225 C;
2
2
3
2
2
3
ꢀ
1
1
IR (KBr) cm : 3290 (NH), 1680 (C = O), 1608 (C = N); H-
3
NMR (CDCl ): d 0.95–1.06 (t, 3H, CH CH CH ), 1.45–1.56
7.64 (d, J = 2.5 Hz, 1H, Ar-H), 7.68 (s, 1H, Ar-H), 7.70 (d,
3
2
2
3
(
t, 2H, CH CH CH ), 1.94 (s, 3H, CH ), 2.31–2.39 (m, 2H,
J = 8.0 Hz, 2H, Ar-H), 8.04 (d, J = 8.0 Hz, 2H, Ar-H), 9.51 (br s,
2
2
3
3
+
CH
2
CH
2
CH
3
), 7.34–7.36 (m, 2H, Ar-H), 7.38 (s, 1H, Ar-H),
1H, NH, D
2
O Exchangeable); MS (m/z): 336 (M ); Anal. Calcd for
7
.41 (d, J = 2.5 Hz, 1H, Ar-H), 7.52 (s, 1H, Ar-H), 7.64
19 20 4 2
C H N O : C, 67.83%; H, 5.99%; N, 16.65%. Found: C,
(
(
d, J = 8.0 Hz, 2H, Ar-H), 8.01 (d, J = 8.0 Hz, 2H, Ar-H), 9.04
67.86%; H, 5.95%; N, 16.60%.
+
br s, 1H, NH, D O Exchangeable); MS (m/z): 320 (M );
2-(N-(4-methyl-benzylidene-hydrazino)-3-propyl-3H-quinazolin-
4-one (SR9). A mixture of 2-hydrazino-3-propyl-3H-quinazolin-
4-one (6) (0.004mol) and 4-methylbenzaldehyde (0.004 mol)
in glacial acetic acid was refluxed for 30 h. The reaction
mixture was poured into ice water. The solid obtained was
2
Anal. Calcd for C H N O: C, 71.22%; H, 6.29%; N,
1
1
9 20 4
7.48%. Found: C, 71.28%; H, 6.27%; N, 17.49%.
-(benzylidene-hydrazino)-3-propyl-3H-quinazolin-4-one
SR5). A mixture of 2-hydrazino-3-propyl-3H-quinazolin-4-
2
(
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet