Med Chem Res (2018) 27:488–496
491
acetone to yield the desired product P216 as white solid.
Yield: 60.3%, M.p: 237–239 °C.
The other compounds P203–P215 and P217–P219 were
prepared in the similar manner.
MHz, CDCl , TMS) δ (ppm): 4.054 (s, 3H, OCH ), 7.149
3
3
(d, 1H, 5-H), 7.168–7.390 (m, 8H, 2 × C H ), 8.375 (dd,
6
4
1
3
1H, 6H), 8.812 (d, 1H, 2-H). C NMR (101 MHz, DMSO-
d6) δ (ppm): 170.1 (C=O), 166.2 (C=O), 162.8, 149.9,
148.3, 135.5, 133.3, 132.6, 126.7, 123.2, 121.5, 120.3,
P203 Yield = 54.00%; M.p: 125–126 °C; MS (m/z): 790.8
115.3, 109.3, 108.6, 54.8 (OCH3).
+
−1
[
2M + Na] ; IR (KBr) cm : 1747.39, 1732.14 (υC=O),
1
610.34 (υC=C), 1500.25 (βAr–H), 1258.25, 1175.65,
P208 Yield = 51.76 %; M.p: 134–135 °C; MS (m/z):
1034.2 [2M + Na] ; IR (KBr) cm : 1725.83 (υC=O),
1616.06, 1584.90 (υC=C), 1498.05, 1472.22 (βArH),
1
+
−1
1
044.32 (υC–O–C), 753.35 (γAr–H); H NMR (400 MHz,
CDCl , tetramethylsilane (TMS)) δ (ppm): 4.054 (s, 3H,
3
OCH ), 7.164 (d, 1H, 5-H), 7.192–7.295 (m, 8H, 2 ×
1280.17, 1218.99, 1190.40, 1086.98 (υC–O–C), 852.32,
3
1
3
1
C H ), 8.415 (dd, 1H, 6-H), 8.925 (d, 1H, 2-H); C NMR
768.91 (γAr–H); H NMR (400 MHz, CDCl , TMS) δ (ppm):
6
4
3
(
(
1
101 MHz, DMSO-d6) δ (ppm): 169.14 (C=O), 166.1
C=O), 162.8, 148.3, 136.5, 132.6, 127.8, 122.6, 121.5,
15.8, 55.7 (OCH3).
4.052 (s, 3H, OCH ), 7.154 (d, 1H, 5-H), 7.180–7.448 (m,
3
8H, 2 × C H ), 8.371 (dd, 1H, 6-H), 8.807 (d, 1H, 2-H).
6
4
1
3
C NMR (101 MHz, DMSO-d6) δ (ppm): 170.1 (C=O),
66.2 (C=O), 164.4, 149.9, 148.3, 135.5, 133.3, 132.6,
1
P204 Yield = 62.58 %; M.p: 115–116 °C; MS (m/z):
126.7, 123.2, 121.5, 120.3, 119.3, 117.8, 54.8 (OCH3).
+
−1
8
56.5 [2M + Na] ; IR (KBr) cm : 1755.82,1742.02
(
1
υC=O), 1609.76 (υC=C), 1476.93 (βAr–H), 1280.56,
199.04, 1071.11 (υC–O–C), 756.97 (γAr–H); H NMR (400
P209 Yield = 41.02 %; M.p: 137–138 °C; MS (m/z): 461
1
+
−1
[M + Na] ; IR (KBr) cm : 1750.19 (υC=O), 1603.28
(υC=C), 1527.73, 1348.95 (υNO2), 1279.78, 1199.88,
MHz, CDCl , TMS) δ (ppm): 4.056 (s, 3H, OCH ), 7.172
(
1
3
3
1
d, 1H, 5H), 7.237–7.504 (m, 8H, 2 × C H ), 8.438 (dd,
1089.29 (υC–O–C), 734.75 (γArH); H NMR (400 MHz,
6
4
1
3
H, 6-H), 8.994 (d, 1H, 2-H); C NMR (101 MHz, DMSO-
CDCl , TMS) δ (ppm): 4.061 (s, 3H, OCH ), 7.184 (d, 1H,
3
3
d6) δ (ppm): 169.3 (C=O), 165.2 (C=O), 163.4, 147.9,
5-H), 7.397–8.171 (m, 8H, 2 × C H ), 8.422 (dd, 1H, 6-H),
6 4
8.963 (d, 1H, 2-H). C NMR (101 MHz, DMSO-d6) δ
1
3
1
48.3, 136.5, 133.3, 132.6, 127.8, 126.7, 123.2, 121.5,
1
20.3, 116.1, 55.8 (OCH3).
(ppm): 169.1 (C=O), 167.2 (C=O), 164.7, 148.9, 148.3,
136.5, 133.3, 132.6, 132.3, 119.3, 117.8, 55.8 (OCH3).
P205 Yield = 43.44 %; M.p: 139–140 °C; MS (m/z):
+
−1
5
(
1
07.1 [2M + Na] ; IR (KBr) cm : 1756.84, 1741.88
P210 Yield = 35.23 %; M.p: 181–182 °C; MS (m/z): 461
-1
υC=O), 1609.68 (υC=C), 1471.94 (βArH), 1279.55, 1196.82,
069.00, 1047.27 (υC–O–C), 756.37 (γAr–H); H NMR (400
MHz, CDCl , TMS) δ (ppm): 4.064 (s, 3H, OCH ), 7.169
[M + Na]+; IR (KBr) cm : 1728.98, 1709.76 (υC=O),
1539.89, 1349.62 (υNO2), 1276.76, 1236.84, 1071.74
(υC–O–C), 812.35, 732.47 (γAr–H); 1H NMR (400 MHz,
1
3
3
(
1
d, 1H, 5-H), 7.192–7.672 (m, 8H, 2 × C H ), 8.455 (dd,
H, 6-H), 9.053 (d, 1H, 2-H). C NMR (101 MHz, DMSO-
CDCl3, TMS) δ (ppm): 4.090 (s, 3H, OCH ), 7.210 (d, 1H,
6
4
3
1
3
5-H), 7.624–8.194 (m, 8H, 2 × C H ), 8.430 (dd, 1H, 6-H),
6
4
d6) δ (ppm): 169.3 (C=O), 165.2 (C=O), 163.7, 147.9,
8.879 (d, 1H, 2-H). 13C NMR (101 MHz, DMSO-d6) δ
(ppm): 172.1 (C=O), 167.2 (C=O), 164.5, 153.3, 148.7,
136.8, 127.6, 125.6, 120.7, 116.3, 55.8 (OCH3).
1
48.3, 136.5, 133.3, 132.6, 127.8, 126.7, 123.2, 121.5,
1
20.3, 115.3, 54.8 (OCH3).
P206 Yield = 49.76%; M.p: 117–118 °C; MS (m/z): 385.2
P211 Yield = 39.27 %; M.p: 210–212 °C; MS (m/z): 461
[M + Na] ; IR (KBr) cm : 1739.32 (υC=O), 1610.49
+
−1
+
−1
[
M + H] ; IR (KBr) cm : 1743.73, 1708.04 (υC=O),
1
1
608.32 (υC=C), 1487.09 (βArH), 1281.63, 1248.90,
(υC=C), 1522.28, 1348.09 (υNO2), 1280.62, 1215.19,
1
1
225.64, 1125.84 (υC–O–C), 770.09, 675.45 (γAr–H);
H
1162.06, 1089.21 (υC–O–C), 866.73, 746.48 (γAr–H);
H
NMR (400 MHz, CDCl , TMS) δ (ppm): 4.054 (s, 3H,
NMR (400 MHz, CDCl , TMS) δ (ppm): 4.083 (s, 3H,
3
3
OCH ), 7.158 (d, 1H, 5-H), 7.364–7.428 (m, 8H, 2 ×
OCH ), 7.204 (d, 1H, 5H), 7.424–7.454, 8.326–8.355 (m,
3
3
1
3
C H ), 8.381 (dd, 1H, 6H), 8.823 (d, 1H, 2-H). C NMR
8H, 2 × C H ), 8.423 (dd, 1H, 6-H), 8.856 (d, 1H, 2-H).
6
4
6 4
1
3
(
(
101 MHz, DMSO-d6) δ (ppm): 170.1 (C=O), 166.2
C=O), 162.8, 149.9, 148.3, 135.5, 133.3, 132.6, 126.7,
C NMR (101 MHz, DMSO-d6) δ (ppm): 170.2 (C=O),
165.6 (C=O), 160.5, 155.6, 154.3, 144.6, 143.2, 136.5,
1
23.2, 121.5, 120.3, 115.3, 109.3, 54.8.
131.6, 125.3, 122.5, 122.3, 117.6, 55.9 (OCH3).
P207 Yield = 53.64 %; M.p: 132–133 °C; MS (m/z):
P212 Yield = 73.94 %; M.p: 157–159 °C; MS (m/z):
838.9 [2M + Na] ; IR (KBr) cm : 1747.18, 1727.14
+
−1
+
−1
8
1
1
56.5 [2M + Na] ; IR (KBr) cm : 1725.93 (υC=O),
591.78 (υC=C), 1498.30 (βAr–H), 1282.56, 1219.33,
(υC=O), 1610.87 (υC=C), 1497.17 (β ), 1168.22, 1109.68,
ArH
1
1
194.02 (υC–O–C), 770.66, 680.20 (γAr–H); H NMR (400
1048.03 (υC–O–C), 757.54 (γArH); H NMR (400 MHz,