Chemistry of Heterocyclic Compounds 2018, 54(5), 554–558
1
3
H Ph); 7.78 (1H, t, J = 7.6, H Ph); 7.58 (2H, d, J = 8.0,
m, H Ph(Ar)). C NMR spectrum, δ, ppm: 90.0 (CN); 97.7
(CN); 114.1; 115.0; 128.6; 130.2; 130.4; 130.5; 130.6;
131.2; 131.7; 132.9; 133.3; 136.2; 142.2; 151.7; 155.7;
157.9; 158.4. Found, %: C 65.68; H 2.57; N 18.34.
H Ar); 7.49 (2H, d, J = 8.0, H Ar); 2.47 (3H, s, CH
3
).
); 89.5 (CN); 96.8
CN); 114.9; 115.9; 128.8; 130.0; 130.1; 130.4; 131.2;
1
3
C NMR spectrum, δ, ppm: 21.5 (CH
3
(
1
1
31.8; 136.0; 141.6; 141.8; 151.6; 156.0; 157.6; 160.5;
72.5. Found, %: C 72.65; H 3.45; N 19.13. C22 O.
C
21
H
10ClN
5
O. Calculated, %: C 65.72; H 2.63; N 18.25.
H
13
N
5
3,8-Bis(4-methylphenyl)-6-oxo-6H-pyrido[1,2-b][1,2,4]-
Calculated, %: C 72.72; H 3.61; N 19.27.
triazine-7,9-dicarbonitrile (8). Yield 0.320 g (85%),
–1
8
-(4-Methoxyphenyl)-6-oxo-3-phenyl-6H-pyrido[1,2-b]-
orange solid, mp 298–302°C (decomp.). IR spectrum, ν, cm :
1
[
1,2,4]triazine-7,9-dicarbonitrile (3). Yield 0.307 g (81%),
1686, 2226. H NMR spectrum, δ, ppm (J, Hz): 9.88 (1H,
–
1
orange solid, mp 320–324°C (decomp.). IR spectrum, ν, cm :
s, N=CH); 8.47 (2H, d, J = 8.0, H Ar); 7.60 (2H, d, J = 8.0,
1
1
677, 2228. H NMR spectrum, δ, ppm (J, Hz): 9.91 (1H,
H Ar); 7.57 (2H, d, J = 8.0, H Ar); 7.49 (2H, d, J = 8.0,
1
3
s, N=CH); 8.56 (2H, d, J = 7.6, H Ph); 7.88 (1H, t, J = 7.2,
H Ph); 7.78 (2H, t, J = 8.0, H Ph); 7.66 (2H, d, J = 8.0,
H Ar); 2.52 (3H, s, CH
3
); 2.47 (3H, s, CH
3
). C NMR
spectrum, δ, ppm: 21.5 (CH
3
); 22.1 (CH ); 89.3 (CN); 96.4
3
H Ar); 7.24 (2H, d, J = 8.0, H Ar); 3.93 (3H, s, OCH
3
).
); 89.5 (CN); 96.6
CN); 114.8; 115.0; 116.1; 125.9; 130.1; 130.4; 130.9;
(CN); 114.9; 115.9; 128.8; 129.1; 130.0; 130.2; 131.1;
131.2; 141.5; 141.9; 147.5; 151.7; 156.0; 157.3; 160.5;
1
3
C NMR spectrum, δ, ppm: 56.0 (OCH
3
(
172.5. Found, %: C 73.34; H 3.86; N 18.63. C23
Calculated, %: C 73.20; H 4.01; N 18.56.
H
15
N O.
5
1
31.8; 136.0; 141.7; 151.6; 156.0; 157.6; 160.1; 161.9.
Found, %: C 69.52; H 3.36; N 18.31. C22
Calculated, %: C 69.65; H 3.45; N 18.46.
H
13
N
5
O
2
.
8-(4-Methoxyphenyl)-3-(4-methylphenyl)-6-oxo-6H-
pyrido[1,2-b][1,2,4]triazine-7,9-dicarbonitrile (9). Yield
0.342 g (87%), orange solid, mp 299–301°C (decomp.).
8
-(4-Chlorophenyl)-6-oxo-3-phenyl-6H-pyrido[1,2-b]-
–1
1
[
1,2,4]triazine-7,9-dicarbonitrile (4). Yield 0.298 g (78%),
IR spectrum, ν, cm : 1685, 2225. H NMR spectrum,
δ, ppm (J, Hz): 9.87 (1H, s, N=CH); 8.48 (2H, d, J = 8.0,
H Ar); 7.65 (2H, d, J = 8.0, H Ar); 7.60 (2H, t, J = 8.0,
–1
orange solid, mp 331–335°C (decomp.). IR spectrum, ν, cm :
1
1
685, 2226. H NMR spectrum, δ, ppm (J, Hz): 9.95 (1H,
s, N=CH); 8.57 (2H, d, J = 7.2, H Ph); 7.88 (1H, t, J = 7.2,
H Ar); 7.23 (2H, d, J = 8.0, H Ar); 3.19 (3H, s, OCH
3
);
);
13
H Ph); 7.81–7.77 (4H, m, H Ph, H Ar); 7.74–7.71 (2H, m,
2.50 (3H, s, CH
56.0 (OCH
3
). C NMR spectrum, δ, ppm: 22.1 (CH
3
13
H Ar). C NMR spectrum, δ, ppm: 89.4 (CN); 96.9 (CN);
3
); 89.3 (CN); 96.2 (CN); 114.8; 115.1; 116.1;
1
1
14.7; 115.6; 129.7; 130.2; 130.5; 130.8; 131.8; 132.9;
36.1; 136.5; 142.1; 151.7; 155.9; 157.8; 159.3. Found, %:
125.9; 129.1; 130.2; 130.8; 131.1; 141.6; 147.5; 151.7; 156.1;
157.3; 160.1; 161.8. Found, %: C 70.14; H 3.56; N 17.66.
C 65.46; H 2.72; N 18.28. C21
C 65.72; H 2.63; N 18.25.
H
10ClN
5
O. Calculated, %:
C
23
H
15
N
5
O . Calculated, %: C 70.22; H 3.84; N 17.80.
2
8-(4-Chlorophenyl)-3-(4-methylphenyl)-6-oxo-6H-
8
-(4-Nitrophenyl)-6-oxo-3-phenyl-6H-pyrido[1,2-b]-
pyrido[1,2-b][1,2,4]triazine-7,9-dicarbonitrile (10). Yield
[
1,2,4]triazine-7,9-dicarbonitrile (5). Yield 0.290 g (85%),
0.350 g (88%), orange solid, mp 326–330°C (decomp.).
–1
–1
1
orange solid, mp 340–345°C (decomp.). IR spectrum, ν, cm :
IR spectrum, ν, cm : 1687, 2228. H NMR spectrum,
δ, ppm (J, Hz): 9.91 (1H, s, N=CH); 8.48 (2H, d, J = 8.0,
H Ar); 7.80–7.77 (2H, m, H Ar); 7.73–7.70 (2H, m, H Ar);
1
1
707, 2226. H NMR spectrum, δ, ppm (J, Hz): 9.98 (1H,
s, N=CH); 8.58 (2H, d, J = 7.2, H Ph); 8.53 (2H, d, J = 8.0,
H Ar); 7.99 (2H, d, J = 8.0, H Ar); 7.89 (1H, t, J = 7.6,
1
3
7.61 (2H, d, J = 8.0, H Ar); 2.50 (3H, s, CH
3
). C NMR
1
3
H Ph); 7.79 (2H, t, J = 7.6, H Ph). C NMR spectrum,
δ, ppm: 89.2 (CN); 96.9 (CN); 114.5; 115.4; 124.7; 130.3;
spectrum, δ, ppm: 22.1 (CH
3
); 89.2 (CN); 96.6 (CN);
114.8; 115.7; 129.1; 129.6; 130.3; 130.8; 131.2; 132.9;
1
1
C
30.5; 130.6; 131.7; 136.2; 140.1; 142.3; 149.4; 151.7;
136.4; 141.9; 147.7; 151.7; 155.9; 157.5; 159.3; 172.5.
55.7; 158.0; 158.5. Found, %: C 63.87; H 2.76; N 21.38.
Found, %: C 66.23; H 3.15; N 17.54. C22
Calculated, %: C 66.42; H 3.04; N 17.60.
H
12ClN O.
5
21
8
H
10
N
6
O . Calculated, %: C 63.96; H 2.56; N 21.31.
3
-(3-Nitrophenyl)-6-oxo-3-phenyl-6H-pyrido[1,2-b]-
3-(4-Methylphenyl)-8-(4-nitrophenyl)-6-oxo-6H-pyrido-
[1,2-b][1,2,4]triazine-7,9-dicarbonitrile (11). Yield 0.355 g
(87%), orange solid, mp 336–340°C (decomp.). IR spectrum,
[
1,2,4]triazine-7,9-dicarbonitrile (6). Yield 0.331 g (84%),
–1
orange solid, mp 301–304°C (decomp.). IR spectrum, ν, cm :
1
–1
1
1
699, 2225. H NMR spectrum, δ, ppm (J, Hz): 9.98 (1H,
ν, cm : 1698, 2227. H NMR spectrum, δ, ppm (J, Hz):
9.94 (1H, s, N=CH); 8.53 (2H, d, J = 8.0, H Ar); 8.49 (2H,
d, J = 8.0, H Ar); 8.00–7.97 (2H, m, H Ar); 7.62 (2H, d,
s, N=CH); 8.60–8.53 (4H, m, H Ph, H Ar); 8.19–8.17 (1H,
m, H Ph(Ar)); 8.02 (1H, t, J = 8.0, H Ph(Ar)); 7.89 (1H, t,
J = 7.6, H Ph(Ar)); 7.79 (2H, t, J = 8.0, H Ph(Ar)).
13
J = 8.0, H Ar); 2.50 (3H, s, CH
δ, ppm: 22.1 (CH
3
). C NMR spectrum,
); 89.0 (CN); 96.5 (CN); 114.5; 115.4;
1
3
C NMR spectrum, δ, ppm: 89.5 (CN); 97.3 (CN); 114.6;
15.5; 123.8; 126.2; 130.3; 130.5; 131.5; 131.7; 135.4;
35.5; 136.2; 142.4; 148.2; 151.7; 155.8; 158.0; 158.1.
3
1
1
124.7; 129.1; 130.4; 130.6; 131.2; 140.2; 142.2; 147.8;
149.4; 151.8; 155.8; 157.7; 158.5. Found, %: C 64.56;
Found, %: C 63.87; H 2.65; N 21.45. C21
H
10
N
6
O
3
.
H 2.78; N 20.43. C22
H 2.96; N 20.58.
H
12
N
6
O . Calculated, %: C 64.71;
3
Calculated, %: C 63.96; H 2.56; N 21.31.
-(3-Chlorophenyl)-6-oxo-3-phenyl-6H-pyrido[1,2-b]-
1,2,4]triazine-7,9-dicarbonitrile (7). Yield 0.352 g (92%),
8
3-(4-Methylphenyl)-8-(3-nitrophenyl)-6-oxo-6H-pyrido-
[1,2-b][1,2,4]triazine-7,9-dicarbonitrile (12). Yield 0.338 g
(83%), orange solid, mp 298–302°C (decomp.). IR spectrum,
[
–1
orange solid, mp 321–326°C (decomp.). IR spectrum, ν, cm :
1
–1
1
1
682, 2230. H NMR spectrum, δ, ppm (J, Hz): 9.97 (1H, s,
ν, cm : 1691, 2228. H NMR spectrum, δ, ppm (J, Hz):
9.94 (1H, s, N=CH); 8.58–8.53 (2H, m, H Ar); 8.49 (2H, d,
J = 8.0, H Ar); 8.18–8.16 (1H, m, H Ar); 8.02 (1H, t,
N=CH); 8.57 (2H, d, J = 8.8, H Ph(Ar)); 7.89 (1H, t, J = 7.8,
H Ph(Ar)); 7.87–7.74 (3H, m, H Ph(Ar)); 7.72–7.62 (3H,
5
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