Molecules 2014, 19
1171
+
5
.21(q, 1H, NH), 5.60 (s, 1H, thiadiaz.), 5.90–7.28 (m, 9H, coum.); MS m/z 502.1[M-H] , (M =
03.5); Anal. Calcd. for C26 S: C, 62.02; H, 4.20; N, 8.35; Found: C, 61.92; H, 4.22; N, 8.30%.
5
21 3 6
H N O
4
5
3
-Hydroxy-3-(4-(2-(7-hydroxy-2-oxo-2H-chromen-4-yl)acetyl)-2-(methylamino)-4H-1,3,4-thiadiazin-
-yl)-2H-chromen-2-one (5f). Pale yellow crystals (68% yield); mp 222 °C; R = 0.44; FT-IR ν
f
max
−1 1
449, 3337, 1707, 1692, 1613, 1560, 1448, 1395, 1269, 1139, 1032, 853, 759 and 693 cm ; H-NMR
) δ (ppm): 2.70 (d, 3H, CH ), 2.85 (s, 2H, CH ), 4.89 (q, 1H, NH), 5.65 (s, 1H, thiadi.),
(DMSO-d
6
3
2
6
.04–7.28 (m, 8H, coum.), 10.80 (s, 1H, OH-7 coum), 15.0 (s, 1H, OH-4 coum); MS m/z 490.1
+
[M-H] , (M = 491.5); Anal. Calcd. for C H N O S: C, 58.65; H, 3.49; N, 8.55; Found: C, 58.62; H,
2
4
17
3
7
3
.52; N, 8.53%.
4
-Hydroxy-3-(4-(2-(7-hydroxy-2-oxo-2H-chromen-4-yl)acetyl)-2-(ethylamino)-4H-1,3,4-thiadiazin-5-
= 0.53; FT-IR νmax 3447,
yl)-2H-chromen-2-one (5g). Pale yellow crystals (72% yield); mp 261 °C; R
413, 2986, 1708, 1688, 1615, 1562, 1550, 1392, 1269, 1139, 1032, 829, 758 and 690 cm ; H-NMR
DMSO-d ) δ (ppm): 1.30 (t, 3H, CH ), 2.69 (q, 2H, CH ), 2.85 (s, 2H, CH ), 5.21 (t, 1H, NH), 5.63 (s,
f
−1 1
3
(
6
3
2
2
1
5
5
H, thiadiaz.), 6-04-7.27 (m, 8H, coum.), 10.86 (s, 1H, OH-7 coum), 15.1 (s,1H, OH-4 coum); MS m/z
+
04.1[M-H] , (M = 505.5); Anal. Calcd. for C25
9.42; H, 3.82; N, 8.34%.
19 3 7
H N O S: C, 59.40; H, 3.79; N, 8.31; Found: C,
4
5
3
-Hydroxy-3-(4-(2-(7-hydroxy-2-oxo-2H-chromen-4-yl)acetyl)-2-(phenylamino)-4H-1,3,4-thiadiazin-
-yl)-2H-chromen-2-one (5h). Pale yellow crystals (85% yield); mp 289 °C; R = 0.65; FT-IR νmax
418, 3184, 1703, 1608, 1548, 1511, 1393, 1322, 1269, 1139, 1034, 852, 758 and 678 cm ; H-NMR
f
−1 1
(
DMSO-d
6
) δ (ppm): 2.85 (s, 2H, CH
2
), 5.62 (s, 1H, thiadiaz.), 6.04–7.27 (m, 13H, coum. and arom.),
+
8
.11 (s, 1H, NH), 15.0 (s, 1H, OH); MS m/z 552.1[M-H] , (M = 553.5); Anal. Calcd. for C29
H
19
N
3
O
7
S:
C, 62.92; H, 3.46; N, 7.59; Found: C, 62.89; H, 3.42; N, 7.53%.
4
-Hydroxy-3-(4-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)-2-(methylamino)-4H-1,3,4-thia-
f
diazin-5-yl)-2H-chromen-2-one (5i). Pale yellow crystals (68% yield); mp 222–223 °C; R = 0.67;
FT-IR νmax 3496, 2674, 1715, 1696, 1614, 1554, 1540, 1394, 1266, 1211, 1148, 867, 759 and 682
−1 1
cm ; H NMR (DMSO-d
6 3 3 2
) δ (ppm): 1.71 (s, 3H, CH ), 2.73 (d, 2H, CH -N), 4.83 (s, 2H, OCH ), 5.20
(
q, 1H, NH), 5.66 (s, 1H, thiadi.), 5.90–7.28 (m, 8H, coum.), 10.86 (s, 1H, OH-7 coum), 14.6 (s, 1H,
+
OH-4 coum), MS m/z 505.1[M-H] , (M = 505.5); Anal. Calcd. for C H N O S: C, 59.40; H, 3.79; N,
2
5
19
3
7
8
.31; Found: C, 59.32; H, 3.81; N, 8.30%.
4
5
3
6
-Hydroxy-3-(4-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)-2-(ethylamino)-4H-1,3,4-thiadiazin-
-yl)-2H-chromen-2-one (5j). Pale yellow crystals (78 % yield); mp 226 °C; R = 0.69; FT-IR νmax
433, 3169, 2707, 1723, 1676, 1611, 1553, 1492, 1391, 1267, 1210, 1143, 1070, 988, 841, 758 and
f
−1 1
81 cm ; H-NMR (DMSO-d
), 4.83 (s, 2H, OCH
21 3 7
5.0 (s, 1H, OH-4 coum); MS m/z 518.1[M-H] , (M = 519.5); Anal. Calcd. for C26H N O S: C, 60.11;
6
3 3
) δ (ppm): 1.24 (s, 3H, CH ), 1.74 (t, 3H, CH ), 2.0 (s, 1H, NH), 2.69
(q, 2H, CH
2
2
), 5.31 (s, 1H, NH), 5.67 (s, 1H, thiadi.), 5.90–7.28 (m, 8H, coum.),
+
1
H, 4.07; N, 8.09; Found: C, 60.12; H, 4.02; N, 8.10%.