Molecules 2014, 19
13715
4
-Chloro-2-(2,3-dihydrobenzo[b][1,4]-dioxan-2-ylmethylthio)-5-methyl-N-[imino-(4-methyl-1-oxo-
1H)-phthalazin-2-yl)methyl]benzenesulfonamide (23). Starting from 15 (0.222 g) with stirring for 5 h,
.126 g (44%) of the title compound 23 was obtained, mp 156–160 °C; IR (KBr) νmax 3331, 3211
(
0
−
1
(
1
NH), 2923, 2847 (C-H), 1666 (C=O), 1637 (NH), 1523, 1494 (C=C, C=N), 1343, 1145 (SO
2
) cm ;
), 3.46–3.49 (m, 2H, SCH ),
), 6.71–6.81 (m, 4H, arom.), 7.74 (s, 1H, H-3),
.78 (s, 1H, H-6), 7.92–8.03 (m, 3H, H-5, H-6, H-7 phthalazine), 8.23–8.27 (d, J = 7.8 Hz, 1H, H-8
H-NMR (200 MHz, DMSO-d
6
) δ 2.20 (s, 3H, CH
3
Ph), 2.47 (s, 3H, CH
3
2
4
.04–4.10 (m, 1H, OCH), 4.35–4.39 (m, 2H, OCH
2
7
phthalazine), 8.94 (s, 1H, C=NH), 9.30 (s, 1H, SO NH); anal. C 54.63, H 4.03, N 9.79% calcd for
2
C
26
H23ClN
4
O
5
S
2
, C 54.68, H 4.06, N 9.81%.
4
-Chloro-5-methyl-2-(4-methylbenzylthio)-N-[imino-(4-methyl-1-oxo-(1H)-phthalazin-2-yl)methyl]-
benzenesulfonamide (24). Starting from 16 (0.200 g) with stirring for 6 h, 0.081 g (30%) of the title
compound 24 was obtained, mp 174–180 °C; IR (KBr) νmax 3372, 3231 (NH), 2921, 2853 (C-H), 1685
−
1 1
(
C=O), 1634 (NH), 1575, 1456 (C=C, C=N), 1344, 1145 (SO
2 6
) cm ; H-NMR (500 MHz, DMSO-d )
δ 2.17 (s, 3H, CH Ph), 2.22 (s, 3H, CH Ph), 2.45 (s, 3H, CH ), 4.27 (s, 2H, SCH ), 7.04–7.06 (d,
3
3
3
2
J = 7.9 Hz, 2H, arom.), 7.29–7.30 (d, J = 7.9 Hz, 2H, arom.), 7.47 (s, 1H, H-3), 7.73 (s, 1H, H-6),
7
1
1
1
.90–8.02 (m, 3H, H-5, H-6, H-7 phthalazine), 8.26–8.28 (d, J = 7.8 Hz, 1H, H-8 phthalazine), 8.89 (s,
13
H, C=NH), 9.26 (s, 1H, SO
27.6, 128.9, 129.6, 129.8, 129.9, 131.4, 132.7, 133.1, 133.7, 135.1, 137.1, 137.2, 137.9, 138.5, 144.9,
55.0, 157.9; anal. C 56.95, H 4.36, N 10.67% calcd for C25 , C 56.97, H 4.40, N 10.63%.
2 6
NH); C-NMR (125 MHz, DMSO-d ) δ 19.1, 19.5, 21.4, 37.1, 126.8, 127.1,
4 3 2
H23ClN O S
4
-Chloro-2-(4-chlorobenzylthio)-5-methyl-N-[imino-(4-methyl-1-oxo-(1H)-phthalazin-2-yl)methyl]-
benzenesulfonamide (25). Starting from 17 (0.210 g) with stirring for 1 h, 0.160 g (53%) of the title
compound 25 was obtained, mp 169–174 °C; IR (KBr) νmax 3230 (NH), 2920 (C-H), 1683 (C=O),
−
1 1
1
634 (NH), 1575, 1487 (C=C, C=N), 1344, 1144 (SO
s, 3H, CH Ph), 2.43 (s, 3H, CH ), 4.33 (s, 2H, SCH ), 7.29–7.30 (d, J = 7.8 Hz, 2H, arom.), 7.43–7.47
m, 3H, H-3, arom.), 7.72 (s, 1H, H-6), 7.90–8.02 (m, 3H, H-5, H-6, H-7 phthalazine), 8.26–8.28 (d,
2 6
) cm ; H-NMR (500 MHz, DMSO-d ) δ 2.16
(
3
3
2
(
1
3
2
J = 7.8 Hz, 1H, H-8 phthalazine), 8.92 (s, 1H, C=NH), 9.27 (s, 1H, SO NH); C-NMR (125 MHz,
DMSO-d
33.2, 135.1, 136.1, 136.5, 137.9, 138.9, 144.9, 155.0, 157.9; anal. C 52.67, H 3.66, N 10.26% calcd
, C 52.65, H 3.68, N 10.23%.
6
) δ 19.1, 19.5, 36.5, 126.8, 127.1, 127.5, 129.0, 129.3, 129.9, 131.4, 131.7, 132.5, 133.0,
1
2 4 3 2
for C24H20Cl N O S
4
-Chloro-5-methyl-2-[(2-phenylsulfonyl)ethylthio]-N-[imino-(4-methyl-1-oxo-(1H)-phthalazin-2-yl)-
methyl]benzenesulfonamide (26). Starting from 18 (0.238 g) with stirring for 3.5 h, 0.190 g (64%) of
the title compound 25 was obtained, mp 193–195 °C; IR (KBr) νmax 3372, 3231 (NH), 2921, 2853 (C-H),
−
1
1
1
685 (C=O), 1634 (NH), 1575, 1456 (C=C, C=N), 1344, 1145 (SO
DMSO-d ) δ 2.13 (s, 3H, CH Ph), 2.45 (s, 3H, CH ), 3.20–3.27 (m, 2H, CH
CH ), 7.45 (s, 1H, H-3), 7.61–7.81 (m, 4H, arom.), 7.89–8.06 (m, 5H, H-5, H-6 and H-7 phthalazine,
arom.), 8.16–8.20 (d, J = 7.8 Hz, 1H, H-8 phthalazine), 8.91 (s, 1H, C=NH), 9.25 (s, 1H, SO NH);
) δ 18.7, 19.6, 26.4, 54.3, 126.4, 126.6, 127.1, 128.0,129.4, 129.9,
30.0, 131.1, 132.7, 133.8, 134.3, 134.4, 134.7, 137.9, 138.6, 139.8, 144.6, 154.6, 157.3; anal. C
0.82, H 3.91, N 9.51% calcd for C25 , C 50.80, H 3.92, N 9.48%.
2
) cm ; H-NMR (200 MHz,
6
3
3
2
), 3.55–3.63 (m, 2H,
2
2
1
3
C-NMR (50 MHz, DMSO-d
6
1
5
4 5 3
H23ClN O S