Chemistry of Heterocyclic Compounds 2020, 56(8), 1078–1091
Phenyl 2-phenyl-6Н-benzo[c]thieno[2,3,4-i,j]-2,7-naph-
thyridine-5-carboxylate (3j). Yield 758 mg (60%), yellow
(C-10b); 140.9 (C-5a); 141.9 (C-6a); 148.7 (C-1 C
6
H
4
CH );
3
160.2 (C-2); 161.4 (C-3a); 161.8 (С=O); 162.8 (C-8). Mass
–1
+
+
crystals, mp 214–216°C (EtOAc). IR spectrum, ν, cm :
spectrum, m/z (Irel, %): 465 [M+H] (21), 464 [M] (97),
1
1
665 (С=О), 3375 (NH). H NMR spectrum (DMSO-d
6
),
358 (12), 357 (100), 329 (44), 43 (66). Found, %: C 72.54;
δ, ppm (J, Hz): 7.17 (1Н, t, J = 7.1, Н-9); 7.23–7.38 (3H,
m, H Ar); 7.40–7.58 (6H, m, H Ar); 7.73 (1H, d, J = 8.3,
H-7); 8.24 (2H, d, J = 6.7, Н-2,6 2-Ph); 8.29 (1H, s, H-1);
H 4.17; N 5.91. C28
H
20
N
2
O S. Calculated, %: C 72.39;
3
H 4.34; N 6.02.
N-Methyl-N,2-diphenyl-6H-benzo[c]thieno[2,3,4-i,j]-
1
3
7
8
.57 (1H, d, J = 7.9, H-10); 10.63 (1H, s, NH). C NMR
spectrum (DMSO-d ), δ, ppm: 106.4 (С-1); 112.0 (С-5);
17.2 (С-10а); 118.7 (С-7); 122.7 (С-2,6 OPh); 123.0
С-9); 123.4 (С-10с); 125.5 (С-10); 126.2 (С-4 OPh);
2,7-naphthyridine-5-carboxamide (3m). Yield 922 mg
6
(71%), bright-yellow crystals, mp 283–285°C (DMSO).
–1
1
1
(
IR spectrum, ν, cm : 1624 (С=О), 3296 (NH). H NMR
3
spectrum (CDCl ), δ, ppm (J, Hz): 3.44 (3H, s, NCH );
3
1
1
1
27.9 (С-2,6 Ph); 129.2 (С-3,5 Ph); 129.8 (С-3,5 OPh);
30.3 (С-4 Ph); 132.7 (С-8); 138.7 (С-1 Ph); 139.7 (С-5а);
40.1 (С-6а); 140.9 (С-10b); 150.9 (С-1 OPh); 160.4
7.05 (1H, d, J = 8.0, H-7); 7.06 (1Н, t, J = 8.0, H-9); 7.35–
7.53 (9Н, m, H Ph, H-8); 7.66 (1Н, s, H-1); 7.90 (1H, d,
J = 8.0, H-10); 7.96 (2H, d, J = 8.3, H-2,6 2-Ph); 10.48 (1H,
(
(
(
(
(
С-2); 161.5 (С-3а); 161.7 (С=О). Mass spectrum, m/z
s, NH). 13C NMR spectrum (CDCl
3
), δ, ppm: 38.5 (NCH );
3
+
+
I
rel, %): 421 [M+H] (13), 420 [M] (48), 217 (100), 328
94.0 (C-5); 105.3 (C-1); 117.1 (C-7); 117.4 (C-10a); 121.1
(C-9); 122.4 (C-10); 124.2 (C-10c); 127.4 (C-2,6 2-Ph);
128.7; (C-2,6 NPh); 129.0 (C-4 NPh); 129.3 (C-4 2-Ph);
129.4 (C-3,5 2-Ph); 130.0 (C-3,5 NPh); 132.0 (C-8); 138.8
(C-10b); 139.7 (C-1 2-Ph); 139.8 (C-6a); 141.1 (C-5а);
142.8 (C-1 NPh); 160.4 (C-2); 162.4 (C-3a); 166.1 (C=O).
25), 327 (100), 301 (11), 299 (53), 298 (16), 265 (10), 255
10), 229 (10), 228 (13), 218 (10), 140 (13), 107 (14), 94
57), 80 (15), 58 (19), 52 (10), 43 (33), 42 (14), 40 (17).
Found, %: C 72.34; H 3.79; N 6.59. C26
H
16
N
2
O S.
2
Calculated, %: C 72.27; H 3.84; N 6.66.
1
5
Phenyl 8-methyl-2-phenyl-6Н-benzo[c]thieno[2,3,4-i,j]-
,7-naphthyridine-5-carboxylate (3k). Yield 885 mg
N NMR spectrum (CDCl ), δ, ppm: –266.2 (N-6); –263.5
3
2
(CON); –102.7 (N-3). Mass spectrum, m/z (Irel, %): 434
+ +
(
68%), yellow crystals, mp 308–310°C (EtOAc). IR spect-
[M+H] (11), 433 [M] (72), 327 (100), 326 (40), 300 (16),
299 (44), 298 (14), 227 (107), 108 (21), 107 (47), 106 (76),
–1
1
rum, ν, cm : 1661 (С=О), 3371 (NH). H NMR spectrum
DMSO-d ), δ, ppm (J, Hz): 2.24 (3H, s, CH ); 6.92 (1H, d,
(
6
3
43 (13). Found, %: C 74.75; H 4.47; N 9.63. C27
H
19
N OS.
3
J = 8.3, H-9); 7.26 (2H, d, J = 8.9, H-2,6 OPh); 7.29 (1H, t,
J = 8.0, H-4 OPh); 7.37 (2Н, dd, J = 8.9, J = 8.0, H-3,5
OPh); 7.40 (1H, s, H-7); 7.48 (2H, dd, J = 8.5, J = 8.0,
H-3,5 2-Ph); 7.53 (1H, t, J = 8.0, H-4 2-Ph); 8.08 (1H, s,
H-1); 8.10 (1H, d, J = 8.3, H-10); 8.18 (2H, d, J = 8.5,
Calculated, %: C 74.80; H 4.42; N 9.69.
N,N,2-Triphenyl-6H-benzo[c]thieno[2,3,4-i,j]-2,7-naph-
7
thyridine-5-carboxamide (3n). Yield 743 mg (50%),
orange crystals, mp 235–237°C (DMSO). IR spectrum,
–1
1
ν, cm : 1623 (С=О), 3308 (NH). H NMR spectrum
1
3
H-2,6 2-Ph); 10.33 (1H, s, NH). C NMR spectrum
DMSO-d ), δ, ppm: 21.8 (CH ); 90.2 (C-5); 105.9 (C-1);
14.8 (C-10a); 118.5 (C-7); 120.5 (C-2,6 OPh); 123.1
(CDCl ), δ, ppm (J, Hz): 6.91 (1H, d, J = 7.6, H-7); 7.03 (1Н,
3
(
6
3
t, J = 7.6, H-9); 7.32 (1H, t, J = 7.6, H-8); 7.36–7.51 (13Н,
m, H Ph); 7.62 (1Н, s, H-1); 7.82 (1H, d, J = 7.6, H-10); 7.98
1
13
(
C-10c); 124.2 (C-9); 125.1 (C-10); 126.1 (C-4 O-Ph);
(2H, d, J = 7.4, H-2,6 2-Ph); 10.46 (1H, s, NH). C NMR
1
1
27.8 (C-2,6 2-Ph); 129.1 (C-3,5 2-Ph); 129.8 (C-3,5 OPh);
30.2 (C-4 2-Ph); 138.8 (C-1 2-Ph); 139.5 (C-5a); 139.9
spectrum (CDCl ), δ, ppm: 94.5 (C-5); 105.3 (C-1); 117.1
3
(C-7); 117.4 (C-10a); 121.9 (C-9); 122.1 (C-10c); 124.1
(C-10); 127.4 (C-2,6 2-Ph); 127.5 (2C-4 NPh); 128.6
(C-3,5 2-Ph); 128.7 (2C-2,6 NPh); 129.4 (C-4 6-Ph); 129.5
(2C-3,5 NPh); 132.0 (C-8); 138.7 (C-10b); 139.4 (C-1
6-Ph); 139.5 (C-6a); 142.4 (C-5a); 142.5 (2C-1 NPh); 160.5
(
C-6a); 140.9 (C-10b); 142.8 (C-8); 150.9 (C-1 OPh);
1
60.1 (C-2); 161.4 (C-3a); 161.7 (С=O). Mass spectrum,
+ +
m/z (Irel, %): 435 [M+H] (18), 434 [M] (57), 341 (100),
3
40 (45), 319 (28), 56 (34). Found, %: C 74.68; H 4.24;
15
N 6.49. C27
N 6.45.
H
18
N
2
O
2
S. Calculated, %: C 74.63; H 4.18;
(C-2); 162.8 (C-3a); 166.4 (C=O). N NMR spectrum
(CDCl ), δ, ppm: –263.7 (N-6); –240.5 (CON);
3
+
4-Methylphenyl
8-methoxy-2-phenyl-6Н-benzo[c]-
–102.9 (N-3). Mass spectrum, m/z (Irel, %): 495 [M] (15), 327
(19), 170 (29), 169 (100), 168 (60), 167 (32), 66 (29), 65 (19),
51 (13), 44 (14). Found, %: C 77.48; H 4.22; N 8.55.
thieno-[2,3,4-i,j]-2,7-naphthyridine-5-carboxylate (3l).
Yield 933 mg (67%), yellow crystals, mp 310–312°C
–
1
(
EtOAc). IR spectrum, ν, cm : 1661 (С=О), 3371 (NH).
C
32
H
21
N OS. Calculated, %: C 77.55; H 4.27; N 8.48.
3
1
H NMR spectrum (DMSO-d
s, CH ); 3.76 (3H, s, OCH ); 6.77 (1H, d, J = 8.0, H-9);
.16 (2H, d, J = 8.3, H-2,6 C CH ); 7.23 (2H, d, J = 8.3,
H-3,5 C CH
6
), δ, ppm (J, Hz): 2.31 (3H,
5-(1-Methyl-1Н-benzimidazol-2-yl)-2-phenyl-6Н-benzo-
3
3
[c]thieno[2,3,4-i,j]-2,7-naphthyridine (3o). Yield 645 mg
(50%), orange crystals, mp 310‒312°C (DMSO). IR spect-
7
6
H
4
3
–1
1
6
H
4
3
); 7.35 (1H, s, H-7); 7.48 (2H, t, J = 8.1,
rum, ν, cm : 1620 (С=О), 3657 (NH). H NMR spectrum
H-3,5 2-Ph); 7.51 (1H, t, J = 8.1, H-4 2-Ph); 8.12 (1H, s,
H-1); 8.20 (1H, d, J = 8.0, H-10); 8.22 (2H, d, J = 8.1, H-2,6
(DMSO-d
6
, 120 °C), δ, ppm (J, Hz): 4.04 (3H, s, NCH );
3
7.12 (1H, dd, J = 8.0, J = 7.8, H-9); 7.26 (1H, dd,
J = 8.1, J = 7.6, H-5 benzimidazole); 7.34 (1H, d, J = 7.7,
H-7); 7.42 (2H, t, J = 7.3, H-3,5 2-Ph), 7.50 (1H, dd,
J = 7.8, J = 7.7, H-8); 7.52 (1H, d, J = 8.3, H-7
benzimidazole); 7.54 (1H, dd, J = 8.3, J = 7.6, H-6
benzimidazole); 7.57 (1H, t, J = 7.3, H-4 2-Ph); 7.70 (1H,
d, J = 8.1, H-4 benzimidazole); 8.14 (1H, s, H-1); 8.22 (2H,
1
3
2
-Ph); 10.43 (1H, s, NH). C NMR spectrum (DMSO-d
6
),
); 92.0 (C-5); 102.0 (C-7);
05.5 (C-1); 110.6 (C-10a); 111.3 (C-9); 122.3 (C-2,6
CH ); 122.7 (C-10c); 126.8 (C-10); 127.8 (C-2,6 2-Ph);
29.1 (C-3,5 2-Ph); 130.1 (C-3,5 C CH ); 135.2 (C-4
CH ); 138.7 (C-1 2-Ph); 139.3 (C-4 2-Ph); 139.7
δ, ppm: 20.9 (CH
3
); 55.8 (OCH
3
1
C
6
H
4
3
1
6
H
4
3
C
6
H
4
3
1
090