Med Chem Res
7
7
3
.31 (d, J = 8.0 Hz, 2H, ArH), 7.28–7.26 (m, 3H, ArH),
122.0(ArC), 114.4(ArC), 114.1(ArC), 102.0(=CH), 55.5
+
.05 (d, J = 8.0 Hz, 2H, ArH), 6.48(s, 1H, ArH), 3.90(s,
(OCH ), 46.9(PhCH ); HRMS (ESI-TOF) (m/z) [M + H]
3
2
1
3
H, –OCH3); C NMR (CDCl , 100 MHz): δ = 182.7
calcd for C H N O 370.1317, found 370.1322.
23 18 2 3
3
(
C=O), 181.1(C=O), 162.1(N–C), 148.5(ArC), 145.3
(
ArC), 141.4(ArC), 138.4(ArC), 136.1(ArC), 135.0(ArC),
1
(
1
29.2(ArC), 129.1(ArC), 129.0(ArC), 127.8(ArC), 127.6
ArC), 127.5(ArC), 124.3(ArC), 121.5(ArC), 121.4(ArC),
14.4(ArC), 113.2(ArC), 103.5(=CH), 55.4(OCH3);
3-Pheny-7-benzylamino-l-isoquinoline-5,8-dione (7j)
1
Red solid; yield 75%; mp 197–198 °C; H NMR (CDCl ,
3
+
HRMS (ESI-TOF) (m/z) [M + H] calcd for C H N O
400 MHz): δ = 9.31 (s, 1H, ArH), 8.36 (s, 1H, ArH), 8.18
(d, J = 8.0 Hz, 2H, ArH), 7.53–7.51 (m, 3H, ArH),
2
2 16 2 3
3
56.1161, found 356.1163.
7.38–7.37 (m, 2H, ArH), 7.36–7.34 (m, 2H, ArH), 7.26 (s,
3
-p-Tolyl-7-phenylamino-isoquinoline-5,8-dione (7g)
1H, ArH), 5.89(s, 1H, ArH), 4.41 (d, J = 4.0 Hz, 2H,
1
3
–
CH –); C NMR (CDCl , 100 MHz): δ = 181.4(C=O),
2 3
1
Red solid; yield 62%; mp 207–209 °C; H NMR (CDCl ,
4
180.1(C=O), 163.7(N–C), 148.4(ArC), 148.0(ArC), 140.0
(ArC), 137.8(ArC), 135.4(ArC), 130.8(ArC), 122.7(ArC),
129.7(ArC), 129.2(ArC), 129.0(ArC), 128.7(ArC), 128.4
(ArC), 127.7(ArC), 127.3(ArC), 127.0(ArC), 126.6(ArC),
3
00 MHz): δ = 9.38 (s, 1H, ArH), 8.36 (s, 1H, ArH), 8.13
(
d, J = 8.0 Hz, 2H, ArH), 7.47 (d, J = 8.0 Hz, 2H, ArH),
7
1
.37–7.35 (m, 3H, ArH), 7.34-7.32 (m, 2H, ArH), 6.51(s,
1
3
H, ArH), 2.47(s, 3H, -CH3); C NMR (CDCl , 100 MHz):
115.4(ArC), 102.1(=CH), 46.9(PhCH ); HRMS (ESI-TOF)
3
2
+
δ = 182.5(C=O), 181.0(C=O), 163.8(N-C), 148.5(ArC),
45.3(ArC), 141.4(ArC), 139.5(ArC), 136.9(ArC), 135.0
ArC), 130.2(ArC), 129.8(ArC), 129.5(ArC), 129.1(ArC),
27.6(ArC), 127.2(ArC), 126.3(ArC), 123.3(ArC), 123.0
ArC), 114.9(ArC), 114.6(ArC), 103.5(=CH), 22.5(CH );
(m/z) [M + H] calcd for C H N O 341.1290, found
2
2 17 2 2
1
(
1
(
340.1209.
3-(4-Methoxy-phenyl)-7-morpholin-4-yl-isoquinoline-5,8-
dione (7k)
3
+
HRMS (ESI-TOF) (m/z) [M+H] calcd for C H N O
2
2 16 2 2
3
40.1212, found 341.1281.
1
Red solid; yield 64%; mp 219–221 °C; H NMR (CDCl ,
3
3
-Phenyl-7-phenylamino-isoquinoline-5,8-dione (7h)
400 MHz): δ = 9.24 (s, 1H, ArH), 8.23 (s, 1H, ArH), 8.16
(
d, J = 8.0 Hz, 2H, ArH), 7.04 (d, J = 8.0 Hz, 2H, ArH),
1
Red solid; yield 65%; mp 183–185 °C; H NMR (CDCl ,
6.10(s, 1H, ArH), 3.94–3.92 (m, 2H, –CH –), 3.90–3.89
3
2
4
00 MHz): δ = 9.39 (s, 1H, ArH), 8.38 (s, 1H, ArH), 8.20
(m, 2H, –CH –), 3.89 (s, 3H, –OCH ), 3.63–3.61 (m, 4H,
2 × –CH –); C NMR (CDCl , 100 MHz): δ = 182.4
2
3
1
2 3
3
(
d, J = 8.0 Hz, 2H, ArH), 7.53 (d, J = 8.0 Hz, 3H, ArH),
7
1
1
.48–7.46 (m, 2H, ArH), 7.31–7.29 (m, 3H, ArH), 6.49(s,
(C=O), 182.0(C=O), 162.3(N–C), 161.9(ArC), 153.4
(ArC), 148.9(ArC), 138.5(ArC), 130.3(ArC), 129.2(ArC),
129.0(ArC), 123.9(ArC), 114.6(ArC), 114.2(ArC), 113.4
(ArC), 111.2(=CH), 66.5(CH ), 66.3(CH ), 55.5(OCH ),
1
3
H, ArH); C NMR (CDCl , 100 MHz): δ = 182.3(C=O),
3
81.1(C=O), 163.8(N–C), 148.5(ArC), 145.3(ArC), 139.6
(
1
(
1
ArC), 137.8(ArC), 136.9(ArC), 130.9(ArC), 129.8(ArC),
29.5(ArC), 129.3(ArC), 129.0(ArC), 127.7(ArC), 127.3
ArC), 126.3(ArC), 123.5(ArC), 123.0(ArC), 122.5(ArC),
15.2(ArC), 103.6(=CH); HRMS (ESI-TOF) (m/z) [M +
2
2
3
+
49.2(CH ), 49.0(CH ); HRMS (ESI-TOF) (m/z) [M+H]
2 2
calcd for C H N O 351.1345, found 351.1334.
20 19 2 4
+
H] calcd for C H N O 326.1055, found 326.1059
2
1 14 2 2
3-p-Tolyl-7-morpholin-4-yl-isoquinoline-5,8-dione (7l)
3
-(4-Methoxy-phenyl)-7-benzylamino-isoquinoline-5,8-
1
dione (7i)
Red solid; yield 69%; mp 213–214 °C; H NMR (CDCl ,
3
4
00 MHz): δ = 9.26 (s, 1H, ArH), 8.26 (s, 1H, ArH), 8.07
1
Red solid; yield 71%; mp 205–207 °C; H NMR (CDCl ,
(d, J = 8.0 Hz, 2H, ArH), 7.33 (d, J = 8.0 Hz, 2H, ArH),
3
4
00 MHz): δ = 9.26 (s, 1H, ArH), 8.28 (s, 1H, ArH), 8.16
6.10(s, 1H, ArH), 3.89–3.87 (m, 4H, 2 × –CH –),
2
1
3
(
d, J = 8.0 Hz, 2H, ArH), 7.40–7.38 (m, 2H, ArH),
3.62–3.60 (m, 4H, 2 × –CH –), 2.45 (s, 3H, –CH );
C
2
3
7
8
2
.36–7.34 (m, 2H, ArH), 7.26 (s, 1H, ArH), 7.03 (d, J =
NMR (CDCl , 100 MHz): δ = 182.4(C=O), 182.0(C=O),
3
.0 Hz, 2H, ArH), 5.87 (s, 1H, ArH), 4.41 (d, J = 8.0 Hz,
162.7(N–C), 153.3(ArC), 148.8(ArC), 141.2(ArC), 138.5
(ArC), 134.9(ArC), 129.8(ArC), 129.6(ArC), 127.5(ArC),
127.3(ArC), 124.4(ArC), 114.1(ArC), 111.2(=CH), 66.4
(CH ), 66.1(CH ), 49.2(CH ), 49.0(CH ), 21.3(CH );
1
3
H, –CH –), 3.89(s, 3H, –OCH ); C NMR (CDCl , 100
2
3
3
MHz): δ = 181.5(C=O), 180.7(C=O), 163.2(N–C), 162.0
ArC), 148.4(ArC), 148.1(ArC), 139.6(ArC), 135.5(ArC),
30.4(ArC), 129.7(ArC), 129.5(ArC), 129.3(ArC), 129.1
ArC), 128.9(ArC), 128.3(ArC), 127.7(ArC), 127.3(ArC),
(
1
(
2
2
2
2
3
+
HRMS (ESI-TOF) (m/z) [M + H] calcd for C H N O
20 19 2 3
335.1396, found 335.1386.