RSC Advances
Paper
40), 7.89–7.80 (m, 4H, ArH), 7.68–7.61 (m, 4H, ArH), 7.48–7.36 (m, 2H, ArH), 6.36–6.29 (m, 2H, ArH), 2.20 (s, 3H, CH3); 13C NMR
(m, 4H, ArH); 13C NMR (75 MHz, DMSO-d6): d 158.8, 158.7, (75 MHz, DMSO-d6): d 170.0, 159.1, 154.2, 150.2, 147.2, 139.0,
155.1, 154.9, 149.2, 149.1, 147.8, 135.6, 135.1, 131.5, 131.3, 132.2, 131.5, 130.6, 128.4, 127.5, 125.9, 124.3, 123.3, 120.1, 118.8,
125.6, 125.5, 123.2, 122.6, 118.6, 118.5, 118.3, 116.7; anal. calcd 116.2, 114.6, 96.3, 23.9; anal. calcd for C29H19N3O5S: C, 66.77; H,
for C28H16ClN3O5S: C, 62.04; H, 2.96; N, 7.73; S, 5.90; found: C, 3.67; N, 8.05; S, 6.13; found: C, 66.69; H, 3.60; N, 8.01; S, 6.09.
62.00; H, 2.90; N, 7.69; S, 5.87.
(E)-N0-(3-(2,3-Dimethylphenyl)-4-(2-oxo-2H-chromen-3-yl)-thia-
(E)-N0-(3-(2-Methoxyphenyl)-4-(2-oxo-2H-chromen-3-yl)thiazol- zol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carbohydrazide
(5i).
2(3H)-ylidene)-2-oxo-2H-chromene-3-carbohydrazide (5d). Yield: Yield: (65%); m.p.: 128–130 ꢂC; Rf: 0.42; IR (ATR, cmꢁ1): 3312
(69%); m.p.: 174–176 C; Rf: 0.42; IR (ATR, cmꢁ1): 3312 (NH), (NH), 1717 (C]O), 1615 (C]N); 1H NMR (300 MHz, DMSO-d6):
ꢂ
1717, 1698 (C]O), 1615 (C]N); 1H NMR (300 MHz, DMSO-d6): d 11.143 (s, 1H, NH), 9.10 (s, 1H, H-4), 8.69 (s, 1H, H-40), 7.96–7.84
d 11.90 (s, 1H, NH), 8.48 (s, 1H, H-4), 8.33 (s, 1H, H-40), 8.32–8.25 (m, 4H, ArH), 7.69–7.49 (m, 4H, ArH), 7.43–7.40 (m, 1H, ArH),
(m, 2H, ArH), 7.90 (t, J ¼ 8.7 Hz, 1H, ArH), 7.28–7.00 (m, 3H, 6.99–6.96 (m, 2H, ArH), 6.65–6.59 (m, 1H, ArH), 2.23 (s, 3H, CH3),
ArH), 6.98–6.96 (m, 3H, ArH), 6.94–6.92 (m, 2H, ArH), 6.89–6.86 2.01 (s, 3H, CH3); 13C NMR (75 MHz, DMSO-d6): d 169.3, 159.7,
(m, 3H, ArH), 3.88 (s, 3H, OCH3); 13C NMR (75 MHz, DMSO-d6): 152.8, 150.3, 147.7, 141.1, 136.8, 131.3, 129.1, 128.4, 127.5, 126.6,
d 169.7, 159.2, 152.7, 147.3, 144.4, 138.4, 138.2, 136.6, 134.4, 125.2, 124.7, 121.0, 120.0, 119.3, 118.3, 116.5, 114.7, 100.2, 23.5,
132.1, 129.2, 128.9126.1, 125.2, 121.1, 119.6, 116.3, 113.2, 111.9, 19.3; anal. calcd for C30H21N3O5S: C, 67.28; H, 3.94; N, 7.84; S,
111.5, 64.5; anal. calcd for C29H19N3O6S: C, 64.79; H, 3.54; N, 5.98; found: C, 67.23; H, 3.90; N, 7.80; S, 5.93.
7.80; S, 5.96; found: C, 64.73; H, 3.49; N, 7.73; S, 5.91.
(E)-N0-(3-(3-Methoxyphenyl)-4-(2-oxo-2H-chromen-3-yl)thiazol- zol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carbohydrazide
(E)-N0-(3-(2,4-Dimethylphenyl)-4-(2-oxo-2H-chromen-3-yl)thia-
(5j).
2(3H)-ylidene)-2-oxo-2H-chromene-3-carbohydrazide (5e). Yield: Yield: (71%); m.p.: 135–137 ꢂC; Rf: 0.43; IR (ATR, cmꢁ1): 3296
(62%); m.p.: 167–169 C; Rf: 0.40; IR (ATR, cmꢁ1): 3332 (NH), (NH), 1717 (C]O), 1612 (C]N); 1H NMR (300 MHz, DMSO-d6):
ꢂ
1721, 1702 (C]O), 1623 (C]N); 1H NMR (300 MHz, DMSO-d6): d 11.02 (s, 1H, NH), 9.09 (s, 1H, H-4), 8.58 (s, 1H, H-40), 7.93–7.87
d 11.67 (s, 1H, NH), 9.15 (s, 1H, H-4), 8.68 (s, 1H, H-40), 8.38–8.27 (m, 2H, ArH), 7.83–7.74 (m, 2H, ArH), 7.61–7.59 (m, 1H, ArH),
(m, 2H, ArH), 7.73–7.62 (m, 4H, ArH), 7.30–7.26 (m, 1H, ArH), 7.37–7.19 (m, 4H, ArH), 6.96–6.91 (m, 1H, ArH), 6.73–6.65 (m,
7.10–6.99 (m, 4H, ArH), 6.38–6.31 (m, 2H, ArH), 3.65 (s, 3H, 2H, ArH), 2.34 (s, 3H, CH3), 2.02 (s, 3H, CH3); 13C NMR (75 MHz,
OCH3); 13C NMR (75 MHz, DMSO-d6): d 169.7, 159.3, 157.1, DMSO-d6): d 168.1, 158.5, 152.0, 151.6, 148.3, 143.8, 139.1, 137.4,
151.6, 150.7, 148.1, 143.9, 132.0, 130.7, 128.1, 126.1, 125.2, 136.3, 133.2, 131.6, 130.4, 129.1, 127.3, 126.7, 125.5, 121.2, 119.3,
124.6, 123.3, 121.7, 120.3, 119.9, 116.6, 111.6, 110.7, 95.8, 56.3; 117.1, 114.7, 100.1, 26.3, 15.8; anal. calcd for C30H21N3O5S: C,
anal. calcd for C29H19N3O6S: C, 64.79; H, 3.54; N, 7.80; S, 5.96; 67.27; H, 3.95; N, 7.83; S, 5.97; found: C, 67.19; H, 3.84; N, 7.76; S,
found: C, 64.71; H, 3.50; N, 7.70; S, 5.89.
5.83.
(E)-N0-(3-(2,6-Dimethylphenyl)-4-(2-oxo-2H-chromen-3-yl)-
(E)-2-Oxo-N0-(4-(2-oxo-2H-chromen-3-yl)-3-o-tolylthiazol-2(3H)-
ylidene)-2H-chromene-3-carbohydrazide (5f). Yield: (67%); m.p.: thiazol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carbohydrazide
109–111 ꢂC; Rf: 0.48; IR (ATR, cmꢁ1): 3381 (NH), 1719, 1699 (C] (5k). Yield: (69%); m.p.: 152–154 ꢂC; Rf: 0.46; IR (ATR, cmꢁ1):
1
O), 1609 (C]N); H NMR (300 MHz, DMSO-d6): d 11.70 (s, 1H, 3316 (NH), 1717 (C]O), 1607 (C]N); 1H NMR (300 MHz,
NH), 8.47 (s, 1H, H-4), 8.10 (s, 1H, H-40), 7.43–7.41 (m, 4H, ArH), DMSO-d6): d 11.11 (s, 1H, NH), 9.39 (s, 1H, H-4), 9.00 (s, 1H,
7.26–7.14 (m, 4H, ArH), 7.00–6.81 (m, 4H, ArH), 2.30 (s, 3H, CH3); H-40), 7.83–7.69 (m, 4H, ArH), 7.54–7.51 (m, 2H, ArH), 7.39–
13C NMR (75 MHz, DMSO-d6): d 167.2, 153.0, 149.6, 146.2, 144.8, 7.34 (m, 3H, ArH), 6.99–6.96 (m, 2H, ArH), 6.67–6.63 (m, 1H,
138.9, 137.0, 134.8, 131.7, 128.9, 127.5, 126.2, 120.7, 119.6, 116.4, ArH), 2.09 (s, 6H, 2 ꢃ CH3); 13C NMR (75 MHz, DMSO-d6):
115.7, 114.6, 111.4, 21.0; anal. calcd for C29H19N3O5S: C, 66.77; H, d 169.9, 157.2, 151.4, 150.3, 149.0, 147.4, 133.5, 130.6, 129.1,
3.67; N, 8.05; S, 6.13; found: C, 66.68; H, 3.60; N, 8.01; S, 6.08.
128.6, 126.9, 125.4, 123.2, 121.7, 119.1, 118.8, 116.3, 114.5,
(E)-2-Oxo-N0-(4-(2-oxo-2H-chromen-3-yl)-3-m-tolylthiazol-2(3H)- 99.0, 17.6; anal. calcd for C30H21N3O5S: C, 67.27; H, 3.95; N,
ylidene)-2H-chromene-3-carbohydrazide (5g). Yield: (63%); m.p.: 7.83; S, 5.97; found: C, 67.20; H, 3.89; N, 7.79; S, 5.86.
113–115 ꢂC; Rf: 0.47; IR (ATR, cmꢁ1): 3398 (NH), 1716, 1705 (C]
(E)-N0-(3-(3,4-Dimethylphenyl)-4-(2-oxo-2H-chromen-3-yl)thia-
(5l).
1
O), 1616 (C]N); H NMR (300 MHz, DMSO-d6): d 11.21 (s, 1H, zol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carbohydrazide
NH), 9.43 (s, 1H, H-4), 8.86 (s, 1H, H-40), 7.86–7.79 (m, 4H, ArH), Yield: (67%); m.p.: 109–111 ꢂC; Rf: 0.42; IR (ATR, cmꢁ1): 3329
7.53–7.35 (m, 5H, ArH), 7.03–6.98 (m, 2H, ArH), 6.66–6.60 (m, 1H, (NH), 1723 (C]O), 1629 (C]N); 1H NMR (300 MHz, DMSO-d6):
ArH), 6.53–6.49 (m, 1H, ArH), 2.12 (s, 3H, CH3); 13C NMR (75 MHz, d 11.14 (s, 1H, NH), 9.01 (s, 1H, H-4), 8.67 (s, 1H, H-40), 7.97–7.92
DMSO-d6): d 169.1, 158.3, 153.6, 151.2, 148.5, 137.2, 132.9, 131.2, (m, 1H, ArH), 7.81–7.69 (m, 2H, ArH), 7.63–7.57 (m, 1H, ArH),
129.1, 128.6, 127.1, 126.0, 124.7, 122.5, 121.7, 119.2, 117.6, 116.1, 7.48–7.20 (m, 4H, ArH), 7.12–7.02 (m, 1H, ArH), 6.99–6.93 (m,
114.3, 111.5, 98.7, 20.1; anal. calcd for C29H19N3O5S: C, 66.77; H, 1H, ArH), 6.89–6.80 (m, 2H, ArH), 2.22 (s, 3H, CH3), 2.10 (s, 3H,
3.67; N, 8.05; S, 6.13; found: C, 66.70; H, 3.62; N, 8.00; S, 6.06.
CH3); 13C NMR (75 MHz, DMSO-d6): d 168.1, 158.2, 151.1, 149.0,
(E)-2-Oxo-N0-(4-(2-oxo-2H-chromen-3-yl)-3-p-tolylthiazol-2(3H)- 147.7, 140.1, 137.8, 131.5, 130.2, 129.6, 127.3, 126.8, 125.2, 123.7,
ylidene)-2H-chromene-3-carbohydrazide (5h). Yield: (68%); m.p.: 121.0, 119.7, 118.4, 116.3, 115.1, 114.8, 99.0, 20.8, 18.1; anal.
108–110 ꢂC; Rf: 0.49; IR (ATR, cmꢁ1): 3410 (NH), 1725, 1707 calcd for C30H21N3O5S: C, 67.26; H, 3.93; N, 7.81; S, 5.96; found:
1
(C]O), 1607 (C]N); H NMR (300 MHz, DMSO-d6): d 11.09 (s, C, 67.20; H, 3.87; N, 7.75; S, 5.89.
1H, NH), 9.68 (s, 1H, H-4), 8.94 (s, 1H, H-40), 7.98–7.84 (m, 4H,
(E)-N0-(3-(3,5-Dimethylphenyl)-4-(2-oxo-2H-chromen-3-yl)thia-
ArH), 7.65–7.62 (m, 2H, ArH), 7.46–7.39 (m, 3H, ArH), 6.99–6.93 zol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carbohydrazide (5m).
89928 | RSC Adv., 2015, 5, 89919–89931
This journal is © The Royal Society of Chemistry 2015