M. Gemili et al. / Journal of Molecular Structure 1196 (2019) 536e546
539
118.3, 111.7, 111.5, 109.3, 34.6, 30.9 (3 x C). HRMS (ESI-TOF-MS, m/z):
2.3.12. (Z)-N-(3-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-
calcd. for C31H25N4O3S [MþH]þ 533.1642; found 533.1652.
4-(2-oxo-2H-chromen-3-yl)thiazol-2(3H)-ylidene)-4-(tert-butyl)
benzamide (7l)
Orange powder. Yield, 0.47 g, 82%. m.p.: 288e290 ꢀC (decomp.).
IR (cmꢁ1): ymax 3370, 3203 (NH2), 1719 (C]O, lactone),1694 (C]O),
2.3.8. (Z)-N-(3-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-
4-(4-cyanophenyl)thiazol-2(3H)-ylidene)-4-methoxybenzamide
(7h)
1646 (C]C). 1H NMR (400 MHz, DMSO‑d6):
d 8.19 (s, 1H, NeH),
8.09-8.06 (m, 2H, AreH), 7.96-7.94 (m, 3H, AreH), 7.87 (d, J ¼ 7.0 Hz,
1H, AreH), 7.81-7.74 (m, 3H, NH and AreH), 7.62-7-58 (m, 1H,
AreH), 7.40-7.31 (m, 5H, AreH and CeH thiazole ring), 1.24 (s, 9H,
C(CH3)3.13C NMR (100 MHz, DMSO‑d6): 181.1 (C]O), 175.6 (C]O),
173.1 (C]O), 168.4 (C]N), 158.1 (C]O), 154.4, 153.2, 147.1, 143.8,
135.4, 134.1, 133.1, 132.7 (2 x C), 132.0, 130.0, 129.0, 128.6 (2 x C),
126.3, 125.8, 124.9 (2 x C), 124.8, 118.3, 118.0, 116.1, 111.4, 110.8, 34.6,
30.9 (3 x C). HRMS (ESI-TOF-MS, m/z): calcd. for C33H26N3O5S
[MþH]þ 576.1588; found 576.1578.
Orange powder. Yield, 0.44 g, 87%. m.p.: 294e296 ꢀC (decomp.).
IR (cmꢁ1): ymax 3395, 3290 (NH2), 2231 (C^N), 1682 (C]O), 1626
(C]C). 1H NMR (400 MHz, DMSO‑d6):
d 8.36 (s, 1H, NeH), 8.09 (d,
J ¼ 7.2 Hz, 1H, AreH), 7.98-7.95 (m, 3H, NeH and AreH), 7.85-7.78
(m, 5H, AreH), 7.54 (d, J ¼ 8.1 Hz, 2H, AreH), 7.32 (s, 1H, CeH
thiazole ring), 6.91 (d, J ¼ 8.6 Hz, 2H, AreH), 3.76 (s, 3H, OCH3).
13C NMR (100 MHz, DMSO‑d6): 180.9 (C]O), 176.0 (C]O), 172.8
(C]O),169.0 (C]N),162.1,147.4,137.5,135.5,135.0,132.9,132.4 (2 x
C), 131.7, 130.6 (2 x C), 130.0, 129.1, 128.4 (2 x C), 126.5, 125.9, 118.3,
113.5 (2 x C), 111.8, 111.5, 109.1, 55.3. HRMS (ESI-TOF-MS, m/z):
calcd. for C28H19N4O4S [MþNa]þ 529.0946; found 529.0962.
2.3.13. (Z)-N-(3-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-
4-(2-oxo-2H-chromen-3-yl)thiazol-2(3H)-ylidene)-4-
methoxybenzamide (7m)
Orange powder. Yield, 0.47 g, 86%. m.p.: 286e288 ꢀC (decomp.).
IR (cmꢁ1): ymax 3377, 3247 (NH2), 1717 (C]O, lactone), 1685 (C]O).
2.3.9. (Z)-N-(3-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-
4-(4-cyanophenyl)thiazol-2(3H)-ylidene)-4-chlorobenzamide (7i)
Brown powder. Yield, 0.47 g, 92%. m.p.: 293e295 ꢀC (decomp.).
IR (cmꢁ1): ymax 3542, 3291 (NH2), 2229 (C^N), 1673 (C]O), 1648
1H NMR (400 MHz, DMSO‑d6):
d 8.10-8.05 (m, 3H, NeH and AreH),
7.97-7.92 (m, 3H, NeH and AreH), 7.86-7.84 (m, 1H, AreH), 7.80-
7.72 (m, 3H, AreH), 7.61-7-58 (m, 1H, AreH), 7.35-7.31 (m, 3H,
AreH and CeH thiazole ring), 6.91 (d, J ¼ 8.8 Hz, 2H, AreH), 3.75 (s,
3H, OCH3). 13C NMR (100 MHz, DMSO‑d6): 181.1 (C]O), 175.6 (C]
O),172.7 (C]O),168.2 (C]N),162.0,158.1 (C]O),153.2,147.1,143.7,
135.4, 133.0, 132.7 (2 x C), 132.0, 130.6 (2 x C), 130.0, 129.3, 129.0,
126.3, 125.8, 124.8, 118.3, 118.0, 116.1, 113.4 (2 x C), 111.5, 110.7, 55.3.
HRMS (ESI-TOF-MS, m/z): calcd. for C30H20N3O6S [MH]þ 550.1073;
found 550.1075.
(C]C). 1H NMR (400 MHz, DMSO‑d6):
d 8.38 (s, 1H, NeH), 8.14-8.00
(m, 3H, AreH), 7.97 (s, 1H, NeH), 7.85-7.75 (m, 5H, AreH), 7.52 (d,
J ¼ 10.9 Hz, 2H, AreH), 7.45 (d, J ¼ 11.2 Hz, 2H, AreH), 7.39 (s, 1H,
CeH thiazole ring). 13C NMR (100 MHz, DMSO‑d6): 181.2 (C]O),
176.3 (C]O), 172.6 (C]O), 170.2 (C]N), 147.9, 138.2, 137.0, 136.1,
135.8, 135.3, 133.5, 133.0 (2 x C), 132.1, 130.9 (2 x C), 130.5, 129.0 (2 x
C), 128.9 (2 x C), 127.0, 126.4, 118.8, 112.0, 111.9, 110.2. HRMS (ESI-
TOF-MS, m/z): calcd. for C27H16ClN4O3S [MþH]þ 511.0632; found
511.0631.
2.3.14. (Z)-N-(3-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-
4-(2-oxo-2H-chromen-3-yl)thiazol-2(3H)-ylidene)-4-
chlorobenzamide (7n)
2.3.10. (Z)-N-(3-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-
4-(4-cyanophenyl)thiazol-2(3H)-ylidene)-2,4-dichlorobenzamide
(7j)
Orange powder. Yield, 0.50 g, 91%. m.p.: 306e309 ꢀC (decomp.).
IR (cmꢁ1): ymax 3385, 3294 (NH2),1712 (C]O, lactone),1694 (C]O),
1644 (C]C). 1H NMR (400 MHz, DMSO‑d6):
d 8.21-8.00 (m, 6H, NH2
Black powder. Yield, 0.51 g, 94%. m.p.: 251e253 ꢀC (decomp.). IR
(cmꢁ1): ymax 3442 (NH2), 2232 (C^N), 1688 (C]O), 1649 (C]C). 1H
and AreH), 7.86-7.84 (m, 1H, AreH), 7.81-7.72 (m, 3H, AreH), 7.62-
7.58 (m, 1H, AreH), 7.46-7.44 (m, 2H, AreH), 7.40 (s, 1H, CeH
thiazole ring), 7.34 (d, J ¼ 8.3 Hz, 2H, AreH). 13C NMR (100 MHz,
DMSO‑d6): 181.0 (C]O), 175.5 (C]O), 172.0 (C]O), 169.0 (C]N),
158.1 (C]O), 153.2, 147.0, 144.1, 136.4, 135.6, 135.4, 133.4, 132.8,
132.7, 132.0, 130.4 (2 x C), 130.0, 129.0, 128.3 (2 x C), 126.4, 125.8,
124.8, 118.3, 117.8, 116.1, 111.2 (2 x C). HRMS (ESI-TOF-MS, m/z):
calcd. for C29H17ClN3O5S [MþH]þ 554.0572; found 554.0580.
NMR (400 MHz, DMSO‑d6):
d
8.39 (s, 1H, NeH), 8.04 (d, J ¼ 7.2 Hz,
1H, AreH), 7.93 (s, 1H, NeH), 7.86-7.74 (m, 6H, AreH), 7.56 (d,
J ¼ 2.0 Hz, 1H, AreH), 7.53 (d, J ¼ 8.4 Hz, 2H, AreH), 7.43 (s, 1H, CeH
thiazole ring), 7.40 (dd, J ¼ 8.4 Hz, 2.0 Hz, 1H, AreH). 13C NMR
(100 MHz, DMSO‑d6): 180.7 (C]O),175.9 (C]O),171.9 (C]O),169.7
(C]N), 147.4, 137.9, 135.6, 135.3, 135.0, 134.6, 133.1, 132.9, 132.6,
132.5 (2 x C), 131.7, 130.1, 129.9, 128.6 (2 x C), 127.1, 126.4, 125.8,
118.3, 111.7, 111.4, 109.9. HRMS (ESI-TOF-MS, m/z): calcd. for
27H15Cl2N4O3S [MþH]þ 545.0242; found 545.0217.
2.3.15. (Z)-N-(3-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-
4-(2-oxo-2H-chromen-3-yl)thiazol-2(3H)-ylidene)-2,4-
dichlorobenzamide (7o)
C
2.3.11. (Z)-N-(3-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-
4-(2-oxo-2H-chromen-3-yl)thiazol-2(3H)-ylidene)-4-
methylbenzamide (7k)
Grayish powder. Yield, 0.55 g, 94%. m.p.: 243e245 ꢀC (decomp.).
IR (cmꢁ1): ymax 3411(NH2), 1716 (C]O, lactone), 1643 (C]C). 1H
NMR (400 MHz, DMSO‑d6):
d 8.62 (s, 1H, NeH), 8.13-7.33 (m, 14H,
Orange powder. Yield, 0.45 g, 84%. m.p.: 305e307 ꢀC (decomp.).
IR (cmꢁ1): ymax 3385, 3294 (NH2),1716 (C]O, lactone),1693 (C]O),
NeH, AreH and CeH thiazole ring). 13C NMR (100 MHz, DMSO‑d6):
It was not obtained good spectrum; HRMS (ESI-TOF-MS, m/z):
calcd. for C29H16Cl2N3O5S [MþH]þ 588.0188; found 588.0214.
1645 (C]C). 1H NMR (400 MHz, DMSO‑d6):
d 8.17-8.05 (m, 3H, NeH
and AreH), 7.91 (d, J ¼ 8.0 Hz, 2H, AreH), 7.86-7.73 (m, 5H, NeH
and AreH), 7.62-7-57 (m, 1H, AreH), 7.36 (s, 1H, CeH thiazole
ring), 7.35-7.31 (m, 2H, AreH), 7.18 (d, J ¼ 8.0 Hz, 2H, AreH), 2.29
(m, 3H, CH3). 13C NMR (100 MHz, DMSO‑d6): 181.1 (C]O), 175.6
(C]O), 173.1 (C]O), 168.5 (C]N), 158.1 (C]O), 153.2, 147.1, 143.8,
141.4, 135.4, 134.1, 133.1, 132.7 (2 x C), 132.0, 130.0, 129.0, 128.8 (2 x
C), 128.7 (2 x C), 126.3, 125.8, 124.8, 118.3, 117.9, 116.1, 111.4, 110.9,
21.1. HRMS (ESI-TOF-MS, m/z): calcd. for C30H20N3O5S [MþH]þ
534.1118; found 534.1137.
2.4. Crystallography
The crystallographic structure of the compound 7a which is
single crystal was determined using a four-circle Rigaku R-AXIS
RAPID-S diffractometer (equipped with a two-dimensional area IP
detector).
Graphite-monochromated
Mo-Ka
radiation
(
l
¼ 0.71073 Å) and oscillation scans technique with
D
w ¼ 5ꢀ for
one image were used for data collection. The lattice parameters