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J=8.3, 1.0 Hz, 1H), 8.25 (dd, J=7.9, 1.4 Hz, 1H), 7.95 (t, J=1.8 Hz,
1H), 7.93–7.89 (m, 1H), 7.74 (s, 2H), 7.71–7.67 (m, 2H), 7.61 (t, J=
7.9 Hz, 1H), 7.49 (d, J=2.0 Hz, 1H), 7.39–7.33 (m, 2H), 7.01 (d, J=
8.4 Hz, 1H), 3.83 (s, 3H), 3.81 ppm (s, 3H). 13C NMR (126 MHz,
[D6]DMSO): d=192.91, 163.84, 151.70, 149.19, 145.68, 139.35,
136.67, 134.00, 133.82, 132.03, 131.18, 130.99, 127.47, 127.28,
126.64, 125.88, 124.38, 124.03, 121.88, 121.09, 111.76, 111.01, 55.87,
55.77 ppm. Elemental analysis calcd (%) for C24H20ClNO4 (421.87): C
68.33, H 4.78, N 3.32; found: C 68.15, H 4.76, N 3.37.
for C25H23NO5 (417.45): C 71.93, H 5.55, N 3.36; found: C 71.84, H
5.67, N 3.39.
(E)-N-{2-[3-(3,4-Dimethoxyphenyl)acryloyl]phenyl}-3-methoxy-
benzamide (32): The title compound was synthesized from 3 and
3-methoxybenzoyl chloride to yield a yellow solid (31%), mp: 153–
1548C. 1H NMR (500 MHz, [D6]DMSO): d=12.37 (s, 1H), 8.56 (dd,
J=8.3, 1.0 Hz, 1H), 8.31 (dd, J=8.0, 1.5 Hz, 1H), 7.82–7.74 (m, 2H),
7.71–7.67 (m, 1H), 7.57–7.54 (m, 1H), 7.53–7.48 (m, 3H), 7.39 (dd,
J=8.4, 2.0 Hz, 1H), 7.35–7.30 (m, 1H), 7.22–7.19 (m, 1H), 7.02 (d,
J=8.4 Hz, 1H), 3.84 (s, 3H), 3.83 (s, 3H), 3.81 ppm (s, 3H). 13C NMR
(126 MHz, [D6]DMSO): d=193.03, 164.93, 159.69, 151.72, 149.19,
145.80, 140.02, 136.10, 134.25, 131.40, 130.25, 127.51, 125.59,
124.45, 123.57, 121.28, 120.91, 119.21, 117.86, 112.88, 111.77,
111.09, 55.89, 55.79, 55.50 ppm. Elemental analysis calcd (%) for
C25H23NO5 (417.45): C 71.93, H 5.55, N 3.36; found: C 71.99, H 5.75,
N 3.32.
(E)-4-Chloro-N-{2-[3-(3,4-dimethoxyphenyl)acryloyl]phenyl}ben-
zamide (28): The title compound was synthesized from 3 and 4-
chlorobenzoyl chloride to yield a yellow solid (63%), mp: 176–
1
1778C. H NMR (500 MHz, [D6]DMSO): d=12.37 (s, 1H), 8.52 (d, J=
8.3 Hz, 1H), 8.30 (d, J=7.1 Hz, 1H), 8.00–7.96 (m, 2H), 7.81–7.73
(m, 2H), 7.71–7.64 (m, 3H), 7.50 (d, J=1.8 Hz, 1H), 7.38 (dd, J=8.3,
1.7 Hz, 1H), 7.33 (t, J=7.6 Hz, 1H), 7.01 (d, J=8.3 Hz, 1H), 3.83 (s,
3H), 3.81 ppm (s, 3H). 13C NMR (126 MHz, [D6]DMSO): d=193.00,
164.11, 151.73, 149.19, 145.81, 139.79, 137.14, 134.19, 133.34,
131.34, 129.18 (2C), 129.13 (2C), 127.47, 125.83, 124.46, 123.74,
121.46, 120.92, 111.76, 111.04, 55.89, 55.77 ppm. Elemental analysis
calcd (%) for C24H20ClNO4 (421.87): C 68.33, H 4.78, N 3.32; found: C
68.00, H 4.77, N 3.29.
(E)-N-{2-[3-(3,4-Dimethoxyphenyl)acryloyl]phenyl}quinoline-3-
carboxamide (33): The title compound was synthesized from 3
and quinolone-3-carbonyl chloride to yield a yellow solid (33%),
mp: 165–1678C. 1H NMR (500 MHz, [D6]DMSO): d=12.34 (s, 1H),
9.38 (d, J=2.3 Hz, 1H), 8.92 (d, J=2.2 Hz, 1H), 8.43 (dd, J=8.3,
1.1 Hz, 1H), 8.24 (dd, J=7.9, 1.4 Hz, 1H), 8.16–8.10 (m, 2H), 7.93–
7.88 (m, 1H), 7.74 (s, 2H), 7.74–7.70 (m, 2H), 7.48 (d, J=2.0 Hz,
1H), 7.39–7.34 (m, 2H), 6.99 (d, J=8.5 Hz, 1H), 3.80 (s, 3H),
3.79 ppm (s, 3H). 13C NMR (126 MHz, [D6]DMSO): d=192.88, 163.94,
151.66, 149.18, 148.84, 148.54, 145.64, 139.15, 136.06, 133.90,
131.82, 131.08, 129.43, 128.98, 127.81, 127.47, 127.38, 127.26,
126.63, 124.33, 124.23, 122.25, 121.26, 111.75, 110.97, 55.85,
55.76 ppm. Elemental analysis calcd (%) for C27H22N2O4 (438.47): C
73.96, H 5.06, N 6.39; found: C 73.83, H 5.15, N 6.40.
(E)-N-{2-[3-(3,4-Dimethoxyphenyl)acryloyl]phenyl}-2-nitrobenza-
mide (29): The title compound was synthesized from 3 and 2-nitro-
benzoyl chloride to yield
a yellow solid (56%), mp: 189–
1908C.1H NMR (500 MHz, [D6]DMSO): d=11.70 (s, 1H), 8.18 (d, J=
8.1 Hz, 1H), 8.14–8.10 (m, 2H), 7.86–7.82 (m, 1H), 7.80–7.74 (m,
2H), 7.71–7.66 (m, 1H), 7.63 (s, 2H), 7.48 (d, J=2.0 Hz, 1H), 7.40–
7.35 (m, 1H), 7.34 (dd, J=8.3, 2.0 Hz, 1H), 7.01 (d, J=8.4 Hz, 1H),
3.82 (s, 3H), 3.81 ppm (s, 3H). 13C NMR (126 MHz, [D6]DMSO): d=
192.60, 163.99, 151.61, 149.16, 147.03, 145.48, 137.99, 134.08,
133.42, 132.11, 131.61, 130.63, 128.65, 128.22, 127.39, 124.60,
124.58, 124.23, 122.39, 121.57, 111.73, 110.93, 55.84, 55.73 ppm. Ele-
mental analysis calcd (%) for C24H20N2O6 (432.43): C 66.66, H 4.66, N
6.48; found: C 66.88, H 4.69, N 6.35.
(E)-N-{2-[3-(3,4-Dimethoxyphenyl)acryloyl]phenyl}-1-naphtha-
mide (34): The title compound was synthesized from 3 and 1-
naphthoyl chloride to yield a pale-yellow solid (58%), mp: 150–
1
1528C. H NMR (500 MHz, DMSO) d: 11.86 (s, 1H), 8.44 (dd, J=8.2,
0.9 Hz, 1H), 8.35–8.32 (m, 1H), 8.19 (dd, J=7.9, 1.5 Hz, 1H), 8.11 (d,
J=8.3 Hz, 1H), 8.04–8.01 (m, 1H), 7.86 (dd, J=7.1, 1.2 Hz, 1H),
7.73–7.67 (m, 2H), 7.64 (d, J=15.6 Hz, 1H), 7.61–7.55 (m, 3H), 7.47
(d, J=2.0 Hz, 1H), 7.39–7.34 (m, 1H), 7.33 (dd, J=8.4, 2.0 Hz, 1H),
6.99 (d, J=8.4 Hz, 1H), 3.81 (s, 3H), 3.80 ppm (s, 3H). 13C NMR
(126 MHz, [D6]DMSO): d=192.79, 167.30, 151.63, 149.20, 145.48,
139.08, 134.22, 133.68, 133.49, 131.09, 130.86, 129.83, 128.55,
127.52, 127.43, 127.31, 126.67, 125.71, 125.31, 125.21, 124.27,
124.07, 122.08, 121.48, 111.77, 111.01, 55.89, 55.78 ppm. Elemental
analysis calcd (%) for C28H23NO4 (437.49): C 76.87, H 5.30, N 3.20;
found: C 76.89, H 5.27, N 3.34.
(E)-N-{2-[3-(3,4-Dimethoxyphenyl)acryloyl]phenyl}-3-nitrobenza-
mide (30): The title compound was synthesized from 3 and 3-nitro-
benzoyl chloride to yield a yellow solid (65%), mp: 185–1868C.
1H NMR (500 MHz, [D6]DMSO): d=12.26 (s, 1H), 8.73–8.71 (m, 1H),
8.48–8.43 (m, 1H), 8.36 (dd, J=7.0, 6.5 Hz, 2H), 8.22 (dd, J=7.9,
1.3 Hz, 1H), 7.87 (t, J=8.0 Hz, 1H), 7.72–7.68 (m, 3H), 7.46 (d, J=
1.9 Hz, 1H), 7.38 (d, J=7.8 Hz, 1H), 7.36–7.33 (m, 1H), 6.99 (d, J=
8.3 Hz, 1H), 3.81 (s, 3H), 3.80 ppm (s, 3H). 13C NMR (126 MHz,
[D6]DMSO): d=192.88, 163.21, 151.67, 149.16, 148.16, 145.58,
138.84, 136.04, 133.83, 133.42, 131.04, 130.78, 127.48, 127.43,
126.66, 124.42, 124.29, 122.37, 122.26, 121.30, 111.74, 110.96, 55.85,
55.76 ppm. Elemental analysis calcd (%) for C24H20N2O6 (432.43): C
66.66, H 4.66, N 6.48; found: C 66.23, H 4.57, N 6.51.
(E)-N-{2-[3-(3,4-Dimethoxyphenyl)acryloyl]phenyl}nicotinamide
(35): The title compound was synthesized from 3 and nicotinoyl
chloride to yield a yellow solid (22%), mp: 192–1948C. 1H NMR
(500 MHz, [D6]DMSO): d=12.30 (s, 1H), 9.14 (dd, J=2.3, 0.8 Hz,
1H), 8.79 (dd, J=4.8, 1.6 Hz, 1H), 8.45 (dd, J=8.3, 1.1 Hz, 1H),
8.31–8.28 (m, 1H), 8.27 (dd, J=7.9, 1.4 Hz, 1H), 7.75 (s, 2H), 7.73–
7.67 (m, 1H), 7.63–7.59 (m, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.39–7.34
(m, 2H), 7.01 (d, J=8.4 Hz, 1H), 3.83 (s, 3H), 3.81 ppm (s, 3H).
13C NMR (126 MHz, [D6]DMSO): d=192.92, 163.81, 152.75, 151.71,
149.18, 148.43, 145.79, 139.29, 135.12, 134.02, 131.18, 130.24,
127.47, 126.66, 124.43, 124.10, 124.02, 121.89, 121.03, 111.76,
110.99, 55.88, 55.77 ppm. Elemental analysis calcd (%) for
C23H20N2O4 (388.42): C 71.12, H 5.19, N 7.21; found: C 70.90, H 5.31,
N 6.94.
(E)-N-{2-[3-(3,4-Dimethoxyphenyl)acryloyl]phenyl}-2-methoxy-
benzamide (31): The title compound was synthesized from 3 and
2-methoxybenzoyl chloride to yield an ochre solid (53%), mp:
138–1398C. 1H NMR (500 MHz, [D6]DMSO): d=12.13 (s, 1H), 8.67
(dd, J=8.4, 0.9 Hz, 1H), 8.15 (dd, J=7.9, 1.5 Hz, 1H), 7.98 (dd, J=
7.8, 1.8 Hz, 1H), 7.70 (d, J=1.8 Hz, 2H), 7.66–7.62 (m, 1H), 7.60–
7.55 (m, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.38 (dd, J=8.4, 2.0 Hz, 1H),
7.30–7.26 (m, 1H), 7.25 (d, J=7.8 Hz, 1H), 7.13–7.08 (m, 1H), 7.02
(d, J=8.4 Hz, 1H), 4.10 (s, 3H), 3.83 (s, 3H), 3.81 ppm (s, 3H).
13C NMR (126 MHz, [D6]DMSO): d=192.58, 163.69, 157.30, 151.65,
149.19, 145.60, 138.96, 133.70, 133.38, 131.49, 130.74, 127.46,
126.66, 124.22, 123.18, 122.07, 121.96, 121.84, 120.94, 112.41,
111.76, 111.14, 56.06, 55.89, 55.77 ppm. Elemental analysis calcd (%)
(E)-N-{2-[3-(3,4-Dimethoxyphenyl)acryloyl]phenyl}-7-methoxy-2-
oxo-2H-chromene-3-carboxamide (36): The title compound was
ChemMedChem 2016, 11, 1 – 15
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