Med Chem Res
MHz, DMSO-d6) δ = 18 (CH3), 67 (CH2), 102 (C9′), 111
(C7′), 112 (C3), 114 (C5), 119 (CH=CH–Ar), 123 (C2,6″),
124-(C4″′), 127 (C6′), 130-(C2,6″′), 131 (C3,5″), 132-(C3,5″′),
133 (C4″), 134-(C1″′), 142 (C1″), 143 (CH=CH–Ar), 153
(C10′), 155 (C4), 160 (C8′), 161 (COcoumarin), 167 (CONH),
188 (CO–Ar).
8.26 (d, 1H, Ar–H), 10.58 (bs, 1H, NH); 13C NMR (100
MHz, DMSO-d6) δ = 19 (CH3), 67 (CH2), 102 (C9′), 112
(C7′), 113 (C3), 114 (C5), 119 (CH=CH–Ar), 126 (C2,6″),
127-(C5″′), 128 (C6′), 129-(C6″′), 130 (C3,5″), 131-(C1″′),
132-(C3″′), 135-(C2″′), 136(C4″), 137-(C4″′), 142 (C1″), 143
(CH=CH–Ar), 153 (C10′), 155 (C4), 160 (C8′), 161
(COcoumarin), 167 (CONH), 188 (CO–Ar).
2-(4-Methyl-2-oxo-2H-chromen-7-yloxy)-N-(4-((E)-3-(4-
methoxyphenyl) acryloyl)phenyl)acetamide (8c) Pale yel-
low powder (3.46 g, 73.77% yield), mp 253–255 °C; IR
(KBr) ʋmax (cm−1) 3332 (NH), 1716 (C=O-coumarin), 1683
(C=O-ketone), 1651 (C=O-amide); 1H NMR (400 MHz,
DMSO-d6) δ (ppm): 2.40 (s, 3H, CH3), 3.82 (s, 3H, OCH3),
4.92 (s, 2H, CH2), 6.24 (s, 1H, H-3 pyran), 7.05–7.08 (m,
2H, Ar–H), 7.65–7.74 (m, 3H, Ar–H), 7.83–7.87 (m, 5H,
Ar–H and CH=CH–Ar), 7.99 (d, 1H, J = 15.6 Hz,
CH=CH–Ar), 8.17 (d, 2H,J = 8.4 Hz, Ar–H), 10.56 (bs, 1H,
NH); 13C NMR (100 MHz, DMSO-d6) δ = 19 (CH3), 61
(OCH3), 67 (CH2), 102 (C9′), 111 (C7′), 112 (C3), 113 (C5),
114 -(C3,5″′), 119 (CH=CH–Ar), 126 (C2,6″), 124-(C2,6″′),
127-(C1″′), 130 (C6′), 132 (C3,5″), 134 (C4″), 142 (C1″), 143
(CH=CH–Ar), 153 (C10′), 155 (C4), 160-(C4″′), 161 (C8′),
167 (COcoumarin), 172 (CONH), 187 (CO–Ar).
2-(4-Methyl-2-oxo-2H-chromen-7-yloxy)-N-(4-((E)-3-
(3,4,5- trimethoxyphenyl)acryloyl)phenyl)acetamide (8f)
Yellow powder (5 g, 94.3% yield), mp 267–268 °C; IR
(KBr) ʋmax (cm−1) 3338 (NH), 1710 (C=O-coumarin),
1
1672 (C=O-ketone), 1654 (C=O-amide); H NMR (400
MHz, DMSO-d6) δ (ppm): 2.41 (s, 3H, CH3), 3.71 (s, 3H,
OCH3), 3.86 (s, 6H, 2OCH3), 4.92 (s, 2H, CH2), 6.24 (s,
1H, H-3 pyran), 7.05–7.23 (m, 4H, Ar–H), 7.66–7.75 (m,
2H, Ar–H and CH=CH–Ar), 7.85 (d, 2H, J = 8.4 Hz,
Ar–H), 7.90 (d, 1H, J = 15.6 Hz, CH=CH–Ar), 8.19 (d,
2H, J = 8.4 Hz, Ar–H), 10.58 (bs, 1H, NH); 13C NMR (100
MHz, DMSO-d6) δ = 18 (CH3), 56, 60 (OCH3), 67 (CH2),
102(C9′), 105-(C2,6″′), 111 (C7′), 112 (C3), 116 (C5), 119
(CH=CH–Ar), 124 (C2,6″), 125 (C6′), 126-(C1″′), 131
(C3,5″), 132 (C4″), 134-(C4″′), 135 (C1″), 143
(CH=CH–Ar), 147 –(C3,5″′), 154 (C10′), 158 (C4), 160
(C8′), 161 (COcoumarin), 167 (CONH), 189 (CO–Ar).
2-(4-Methyl-2-oxo-2H-chromen-7-yloxy)-N-(4-((E)-3-(2-
methoxyphenyl)acryloyl)phenyl)acetamide (8d) Pale yel-
low powder (3.33 g, 71% yield), mp 233–234 °C; IR (KBr)
ʋmax (cm−1) 3354 (NH), 1714 (C=O-coumarin), 1695
2-(4-Methyl-2-oxo-2H-chromen-7-yloxy)-N-(4-((E)-3-(4-
chlorophenyl)acryloyl)phenyl)acetamide (8g) Pale yellow
powder (3.5 g, 73.99% yield), mp 240–242 °C; IR (KBr)
ʋmax (cm−1) 3346 (NH), 1703 (C=O-coumarin), 1685
1
(C=O-ketone), 1651 (C=O-amide); H NMR (400 MHz,
DMSO-d6) δ (ppm): 2.41 (s, 3H, CH3), 3.90 (s, 3H, OCH3),
4.92 (s, 2H, CH2), 6.24 (s, 1H, H-3 pyran), 7.04–7.31 (m,
4H, Ar–H), 7.45–7.75 (m, 2H, Ar–H), 7.83 (d, 2H, J = 8.8
Hz, Ar–H), 7.89 (d, 1H, J = 16 Hz, CH=CH–Ar), 7.97 (d,
1H, J = 7.6 Hz, Ar–H), 8.04 (d, 1H, J = 16 Hz,
CH=CH–Ar), 8.15 (d, 2H, J = 8.4 Hz, Ar–H), 10.55 (bs,
1H, NH); 13C NMR (100 MHz, DMSO-dd) δ = 19 (CH3),
61 (OCH3), 67 (CH2), 102 (C9′), 111 (C7′), 112 (C3), 113
(C5), 114-(C3″′), 119-(C1″′), 121-(C5″′), 122 (CH=CH–Ar),
123 (C2,6″), 126-(C6″′), 128 (C6′), 130-(C4″′), 132 (C3,5″),
133 (C4″), 138 (C1″), 143 (CH=CH–Ar), 153 (C10′), 155
(C4), 158-(C2″′), 160 (C8′), 161 (COcoumarin), 167 (CONH),
188 (CO–Ar).
1
(C=O-ketone), 1656 (C=O-amide); H NMR (400 MHz,
DMSO-d6) δ (ppm): 2.41 (s, 3H, CH3), 4.92 (s, 2H, CH2),
6.24 (s, 1H, H-3 pyran), 7.08–7.09 (m, 2H, Ar–H), 7.53 (d,
2H, Ar–H), 7.70–7.75 (m, 2H, Ar–H and CH=CH–Ar),
7.84 (d, 2H, J = 8.8 Hz, Ar–H), 7.93 (d, 2H, J = 8.4,
Ar–H), 7.98 (d, 1H, J = 16 Hz, CH=CH–Ar) 8.18 (d, 2H, J
= 8.4 Hz, Ar–H), 10.56 (bs, 1H, NH); 13C NMR (100 MHz,
DMSO-d6) δ = 18 (CH3), 67 (CH2), 102 (C9′), 111 (C7′),
112 (C3), 114 (C5), 119 (CH=CH–Ar), 123 (C2,6″), 127
(C6′), 129-(C2,6″′), 130-(C3,5″′), 131 (C3,5″), 133-(C1″′), 134
(C4″),135-(C4″′), 142 (C1″), 143 (CH=CH–Ar), 153 (C10′),
155 (C4′), 160 (C8′), 161 (COcoumarin), 167 (CONH), 188
(CO–Ar).
2-(4-Methyl-2-oxo-2H-chromen-7-yloxy)-N-(4-((E)-3-(2,4-
dichlorophenyl)acryloyl)phenyl)acetamide (8e) Pale yel-
low powder (3.74 g, 73.62 % yield), mp 280–281 °C; IR
(KBr) ʋmax (cm−1) 3396 (NH), 1724 (C=O-coumarin),
2-(4-Methyl-2-oxo-2H-chromen-7-yloxy)-N-(4-((E)-3-
(furan-2-yl)acryloyl)phenyl)acetamide (8h) Pale brown
powder (3.46 g, 80.65% yield), mp 228–230 °C; IR (KBr)
ʋmax (cm−1) 3346 (NH), 1734 (C=O-coumarin), 1683
1
1705 (C=O-ketone), 1662 (C=O-amide); H NMR (400
1
MHz, DMSO-d6) δ (ppm): 2.40 (s, 3H, CH3), 4.92 (s, 2H,
CH2), 6.24 (s, 1H, H-3 pyran), 7.05–7.08 (m, 2H, Ar–H),
7.55–7.76 (m, 3H, Ar–H), 7.84 (d, 2H, J = 8.8 Hz, Ar–H),
7.95 (d, 1H, J = 15.6 Hz, –CH=CH–Ar), 8.05 (d, 1H, J =
16.4 Hz, –CH=CH–Ar), 8.20 (d, 2H, J = 8.8 Hz, Ar–H),
(C=O-ketone), 1654 (C=O-amide); H NMR (400 MHz,
DMSO-d6) δ (ppm): 2.40 (s, 3H, CH3), 4.92 (s, 2H, CH2),
6.24 (s, 1H, H-3 pyran), 6.69 (s, 1H, Ar–H), 7.04–7.10 (m,
3H, Ar–H), 7.56 (s, 2H, Ar–H), 7.73 (d, 1H, J = 8.4 Hz,
CH=CH–Ar) 7.81–7.91 (m, 3H, Ar–H and CH=CH–Ar),