J IRAN CHEM SOC
of reaction (checked by TLC), the solvent was evaporated
under vacuum, the obtained solid was washed with water,
and then recrystallized from EtOH to give pure product 3.
(125 MHz, DMSO-d6): 191.5, 160.9, 159.7, 157.1, 153.5,
147.0, 145.5, 143.3, 136.5, 132.8, 132.4, 132.0, 129.6,
126.1, 125.3, 119.9, 119.7, 119.1, 118.3, 116.2. Anal.
Calcd for C24H14BrNO6: C, 58.56; H, 2.87; N, 2.85. Found:
C, 58.70; H, 2.71; N, 2.69.
(E)-3-(3-(4-(4-Nitrophenoxy)phenyl)acryloyl)-2H-
chromen-2-one (3a)Yellow solid; yield: 80 %, mp >250 °C.
IR (KBr): 1703, 1646, 1550, 1348 cm−1 1H NMR
.
(E)-3-(3-(3-Ethoxy-4-(4-nitrophenoxy)phenyl)acryloyl)-
2H-chromen-2-one (3e) Yellow solid; yield: 78 %,
(500 MHz, DMSO-d6): 8.64 (s, 1H, H4), 8.29 (d, J = 7.0,
2H, H3″, H5″), 8.07–8.01 (m, 3H, H2׳
, H6׳
, CH), 7.94 (dd,
J = 8.0, 2.0 Hz, 1H, H5), 7.75 (td, J = 8.0, 2.0 Hz, 1H,
H7), 7.45 (d, J = 8.0 Hz, 1H, H8), 7.42 (t, J = 8.0 Hz, 1H,
H6), 7.34 (d, J = 8.5, 2H, H3′, H5′), 7.31–7.29 (m, 3H, H2″,
H6″, CH). 13C NMR (125 MHz, DMSO-d6): 191.6, 161.0,
159.8, 158.3, 154.5, 146.9, 143.3, 134.4, 132.8, 132.1,
130.7, 128.9, 126.2, 124.9, 124.4, 119.7, 119.3, 119.1,
118.1, 116.0. Anal. Calcd for C24H15NO6: C, 69.73; H,
3.66; N, 3.39. Found: C, 69.54; H, 3.81, N, 3.50.
1
mp >250 °C. IR (KBr): 1708, 1642, 1546, 1370 cm−1. H
NMR (500 MHz, DMSO-d6): 8.59 (s, 1H, H4), 8.23 (d,
J = 7.0, 2H, H3″, H5″), 7.95 (dd, J = 7.5, 2.0 Hz, 1H, H5),
7.76–7.73 (m, 2H, H7, CH), 7.68 (d, J = 1.5 Hz, 1H, H2′),
7.64 (d, J = 8.0, 2.0 Hz, 1H, H6′), 7.45 (d, J = 8.0, 1H,
H5′), 7.43–7.40 (m, 3H, H8, H6, CH), 7.11 (d, J = 7.0 Hz,
2H, H2″, H6″), 4.12 (q, J = 7.0 Hz, 2H, CH2), 1.15 (t,
J = 7.0 Hz, 3H, CH3). 13C NMR (125 MHz, DMSO-d6):
191.8, 162.2, 158.9, 155.3, 154.6, 150.7, 147.4, 146.9,
142.4, 134.6, 134.4, 130.7, 126.2, 125.9, 124.9, 124.2,
124.1, 122.5, 118.1, 116.7, 116.0, 113.9, 64.3, 14.2. Anal.
Calcd for C26H19NO7: C, 68.27; H, 4.19; N, 3.06. Found:
C, 68.41; H, 4.32; N, 3.24.
(E)-8-Methoxy-3-(3-(4-(4-nitrophenoxy)phenyl)acryloyl)-
2H-chromen-2-one (3b) Yellow solid; yield: 75 %,
1
mp >250 °C. IR (KBr): 1708, 1635, 1564, 1358 cm−1. H
NMR (500 MHz, DMSO-d6): 8.58 (s, 1H, H4), 8.28 (d,
J = 7.5 Hz, 2H, H3″, H5″), 8.00 (m, 3H, H2′, H6′, CH), 7.45
(dd, J = 8.0, 2.0 Hz, 1H, H5), 7.39 (dd, J1 = 8.0, 2.0 Hz,
1H, H7), 7.33–7.28 (m, 6H, H6, CH, H3′, H5′, H2″, H6″), 3.92
(s, 3H, OCH3). 13C NMR (125 MHz, DMSO-d6): 191.6,
161.0, 159.8, 158.1, 147.1, 146.2, 143.7, 132.8, 132.1,
129.1, 126.2, 124.8, 124.5, 121.6, 120.5, 120.1, 119.8,
119.1, 118.6, 116.4, 56.2. Anal. Calcd for C25H17NO7: C,
67.72; H, 3.86; N, 3.16. Found: C, 67.55; H, 3.75; N, 3.31.
(E)-3-(3-(3-Ethoxy-4-(4-nitrophenoxy)phenyl)acryloyl)-8-
methoxy-2H-chromen-2-one (3f) Yellow solid; yield: 73 %,
1
mp >250 °C. IR (KBr): 1704, 1637, 1566, 1337 cm−1. H
NMR (500 MHz, DMSO-d6): 8.61 (s, 1H, H4), 8.25–8.23
(m, 3H, H3″, H5″, CH), 7.68 (d, J = 2.0 Hz, 1H, H2′), 7.64
(m, 2H, H6′, CH), 7.48 (dd, J = 7.7, 1.0 Hz, 1H, H5), 7.43–
7.41 (m, 2H, H6, H7), 7.35 (d, J = 8.0, 1H, H5′), 7.11 (d,
J = 9.0 Hz, 2H, H2″, H6″), 4.12 (q, J = 7.0 Hz, 2H, CH2),
3.93 (s, 3H, OCH3), 1.25 (t, J = 7.0 Hz, 3H, CH3). 13C
NMR (125 MHz, DMSO-d6): 191.9, 162.2, 158.1, 157.0,
150.7, 147.4, 147.2, 146.3, 142.4, 134.6, 126.3, 126.2,
125.9, 124.8, 124.5, 124.1, 122.6, 121.6, 118.6, 116.7,
116.5, 113.9, 64.3, 56.2, 14.2. Anal. Calcd for C27H21NO8:
C, 66.53; H, 4.34; N, 2.87. Found: C, 66.38; H, 4.18; N,
2.70.
(E)-7-Methoxy-3-(3-(4-(4-nitrophenoxy)phenyl)
acryloyl)-2H-chromen-2-one (3c) Yellow solid; yield:
70 %, mp >250 °C. IR (KBr): 1700, 1633, 1550,
1350 cm−1 1H NMR (500 MHz, DMSO-d6): 8.61
.
(s, 1H, H4), 8.40–8.29 (m, 3H, H3″, H5″, CH), 8.01 (d,
J = 8.5 Hz, 2H, H2′, H6′), 7.85 (d, J = 8.0 Hz, 1H, H5),
7.33 (d, J = 8.5 Hz, 2H, H3′, H5′), 7.29 (d, J = 9.0 Hz,
2H, H2″, H6″), 7.03–7.02 (m, 2H, H8, CH), 6.99 (dd,
J = 8.0, 2.0 Hz, 1H, H6), 3.91 (s, 3H, OCH3). 13C NMR
(125 MHz, DMSO-d6): 191.5, 164.8, 160.9, 159.7, 158.7,
157.0, 147.5, 143.4, 132.8, 132.1, 132.0, 130.0, 126.1,
120.3, 119.7, 119.6, 119.1, 113.3, 111.7, 100.2, 56.2.
Anal. Calcd for C25H17NO7: C, 67.72; H, 3.86; N, 3.16.
Found: C, 67.86; H, 3.98; N, 3.24.
(E)-3-(3-(3-Ethoxy-4-(4-nitrophenoxy)phenyl)acryloyl)-
7-methoxy-2H-chromen-2-one (3 g) Yellow solid;
yield: 76 %, mp >250 °C. IR (KBr): 1705, 1642, 1556,
1
1350 cm−1. H NMR (500 MHz, DMSO-d6): 8.60 (s, 1H,
H4), 8.23 (d, J = 9.0 Hz, 2H, H3″, H5″), 7.85 (d, J = 9.0 Hz,
1H, H5), 7.67 (s, 1H, H2′), 7.64–7.63 (m, 2H, H6′, CH),
7.41 (d, J = 8.0 Hz, 1H, H5′), 7.11 (d, J = 9.0 Hz, 2H,
H2″, H6″), 7.03 (s, 1H, H8), 7.01–6.99 (m, 2H, H6, CH),
4.12 (q, J = 7.0 Hz, 2H, CH2), 3.90 (s, 3H, OCH3), 1.15
(t, J = 7.0 Hz, 3H, CH3). 13C NMR (125 MHz, DMSO-
d6): 191.7, 164.7, 162.1, 158.7, 157.0, 150.7, 147.4, 147.3,
142.3, 135.0, 134.6, 132.0, 126.5, 125.8, 124.0, 122.5,
120.3, 116.6, 113.8, 113.3, 111.7, 100.1, 64.3, 56.1, 14.1.
Anal. Calcd for C27H21NO8: C, 66.53; H, 4.34; N, 2.87.
Found: C, 66.70; H, 4.51; N, 2.67.
(E)-6-Bromo-3-(3-(4-(4-nitrophenoxy)phenyl)acryloyl)-
2H-chromen-2-one (3d) Yellow solid; yield: 73 %,
1
mp >250 °C. IR (KBr): 1693, 1640, 1566, 1358 cm−1. H
NMR (500 MHz, DMSO-d6): 8.65 (s, 1H, H4), 8.29 (d,
J = 7.0 Hz, 2H, H3″, H5″), 8.19 (d, J = 2.0 Hz, 1H, H5),
8.02–8.00 (m, 3H, H2′, H6′, CH), 7.87 (dd, J = 8.0, 2.0 Hz,
1H, H7), 7.42 (d, J = 8.0 Hz, 1H, H8), 7.33 (d, J = 9.0 Hz,
2H, H3′, H5′), 7.30–7.29 (m, 3H, H2″, H6″, CH). 13C NMR
1 3