Chemistry - A European Journal
10.1002/chem.201905283
FULL PAPER
isomer δ 11.06 (d, J = 7.3 Hz, 1H, NH), 9.77 (s, 1H), 9.44 (s, 1H), 7.64 (d,
(Z)-2-((3-oxo-2-(thiophen-2-yl)prop-1-en-1-yl)amino)benzaldehyde
(3l): Off-white solid, (0.064 g, 0.25 mmol, 69%), 1H NMR (600 MHz,
J = 7.5 Hz, 1H), 7.59 (d, J = 4.3 Hz, 1H), 7.56-7.55 (m, 1H), 7.34 (d, J =
4
2
.8 Hz, 1H), 7.30-7.29 (m, 2H), 7.27-7.26 (m, 2H), 7.09 (t, J = 4.2 Hz, 1H),
.36 (s, 3H); minor isomer δ 13.33 (d, J = 6.8 Hz, 1H), 9.99 (s, 1H), 9.80
CDCl
7.62 (m, 3H), 7.48-7.46 (m, 2H), 7.42 (d, J = 8.5 Hz, 1H), 7.24 (t, J = 4.7
Hz, 1H), 7.20 (t, J = 7.4 Hz, 1H); 13C NMR (150 MHz, CDCl
): δ 194.4,
188.8, 144.0, 142.0, 136.7, 136.5, 136.1, 126.9, 126.5, 126.1, 122.3, 121.5,
3
): δ 11.40 (d, J = 13.0 Hz, 1H, NH), 9.89 (s, 1H), 9.44 (s, 1H), 7.70-
(
d, J = 1.7 Hz, 1H), 7.66 (d, J = 4.4 Hz, 1H), 7.53-7.51 (m, 1H), 7.22-7.21
m, 2 H), 7.18-7.16 (m, 2H), 7.13 (t, J = 4.3 Hz, 1H); rest of the peaks are
3
(
merged; 13C NMR (150 MHz, CDCl
): major isomer δ 194.4, 189.7, 142.3,
38.0, 136.6, 136.0, 129.8, 129.1, 121.2, 112.9; minor isomer δ 193.0,
91.4,138.5, 136.5, 135.4, 129.6, 126.8, 121.2, 113.3, other peaks are
[M+H]: 266.1181, found: 266.1180.
E)-2-((2-(4-chlorophenyl)-3-oxoprop-1-en-1-yl)amino)benzaldehyde
113.2, one peak is merged. ESI-MS calcd for C14
258.0589, found: 258.0602.
3
2
H12NO S [M+H]:
1
1
(E)-2-((3-oxo-2-(thiophen-3-yl)prop-1-en-1-yl)amino)benzaldehyde
(3m): Off-white solid, (0.068 g, 0.26 mmol, 73%), 1H NMR (600 MHz,
merged. ESI-MS calcd for C17H16NO
2
(
(
3
CDCl ): δ 11.23 (d, J = 12.8 Hz, 1H, NH), 9.85 (s, 1H), 9.45 (s, 1H), 7.66-
1
3g): Yellow solid, (0.072 g, 0.25 mmol, 86%), H NMR (600 MHz, CDCl
3
):
7.65 (m, 2H), 7.63-7.59 (m, 2H), 7.49-7.48 (m, 1H), 7.38 (d, J = 8.5 Hz,
1H), 7.35 (dd, J = 3.7, 1.3 Hz, 1H), 7.16 (t, J = 7.3 Hz, 1H); 13C NMR (150
δ 11.14 (d, J = 16.0 Hz, 1H, NH), 9.81 (s, 1H), 9.45 (s, 1H), 7.70-7.61 (m,
H), 7.49-7.47 (m, 2H), 7.37 (s, 3H), 7.16 (s, 1H); 13C NMR (150 MHz,
CDCl ): δ 194.5,189.2, 144.8,142.0, 136.6, 136.1, 134.0, 130.7, 129.3,
22.0, 121.3, 120.8, 112.9 other peaks are merged. ESI-MS calcd for
13NClO [M+H]: 286.0635, found: 286.0638.
E)-2-((2-(4-(tert-butyl)phenyl)-3-oxoprop-1-en-1-
yl)amino)benzaldehyde (3h): Yellow solid, (0.052 g, 0.17 mmol, 64%),
1H NMR (600 MHz, CDCl
): major isomer δ 11.10 (d, J = 13.1 Hz, 1H, NH),
.82 (s, 1H), 9.48 (s, 1H), 7.66 (d, J = 13.3 Hz, 1H), 7.63-7.62 (m, 1H),
.59 (td, J = 7.9, 1.1 Hz, 1H), 7.55-7.53 (m, 2H), 7.38-7.36 (m, 3H), 7.13
3
3
MHz, CDCl ): major isomer δ 194.4, 189.4, 142.1, 136.6, 136.1, 127.6,
3
126.0, 124.3, 121.9, 121.1, 112.9; minor isomer 192.9, 190.5, 137.8, 136.5,
135.4, 130.7, 126.4, 126.3, 122.2, 113.3, other peaks are merged. ESI-MS
1
16
C H
2
2
calcd for C14H12NO S [M+H]: 258.0589, found: 258.0587.
(
(E)-2-((2-(naphthalen-2-yl)-3-oxoprop-1-en-1-yl)amino)benzaldehyde
1
(3n): Yellow solid, (0.071 g, 0.24 mmol, 86%), H NMR (600 MHz, CDCl
3
):
3
δ 11.25 (d, J = 13.0 Hz, 1H, NH), 9.74 (s, 1H), 9.55 (s, 1H), 7.97 (d, J =
8.5 Hz, 1H), 7.93 (s,1H), 7.90-7.89 (m, 1H), 7.87-7.85 (m, 1H), 7.76 (d, J
= 13.2 Hz, 1H), 7.60-7.57 (m, 2H), 7.52 (d, J = 8.7 Hz, 1H), 7.50-7.49 (m,
2 H), 7.39 (d, J = 8.3 Hz, 1H), 7.12 (t, J = 7.5 Hz, 1H); 13C NMR (150 MHz,
9
7
(
t, J = 7.4 Hz, 1H), 1.36 (s, 9H); minor isomer δ 10.03 (s, 1H), 9.86 (d, J =
.4 Hz, 1H), 7.70 (dd, J = 6.1, 1.6 Hz, 1H), 7.43-7.42 (m, 1H), 7.31-7.30
m, 1H), 7.17 (t, J = 7.4, 1H), 1.34 (s, 9H); 13C NMR (150 MHz, CDCl
):
major isomer δ 194.3, 189.9, 151..0, 144.3, 142.3, 136.6, 135.9, 128.7,
3
CDCl
128.6, 128.5, 128.1, 127.8, 126.8, 126.3, 126.2, 121.8, 121.7, 121.3, 112.9.
ESI-MS calcd for C20 [M+H]: 302.1181, found: 302.1178.
3
): δ 194.3, 189.7, 144.7, 142.1, 136.5, 136.0, 133.6, 133.0, 128.7,
(
3
H
16NO
2
1
1
2
3
26.6, 125.9, 121.7, 121.3, 113.3, 113.0, 34.7, 31.3; minor isomer 192.9,
91.3, 138.4, 135.4, 135.2, 127.9, 125.8, 125.0, 122.1, 121.3, 32.2, 26.4,
(E)-5-methyl-2-((2-methyl-3-oxobut-1-en-1-yl)amino)benzaldehyde
1
(4a): Yellow solid, (0.092 g, 0.42 mmol, 71%), H NMR (600 MHz, CDCl
3
):
3.4; other peaks are merged. ESI-MS calcd for C20
H
22NO
2
[M+H]:
δ 10.40 (d, J = 12.2 Hz, 1H), 9.88 (s, 1H), 7.87 (d, J = 12.7 Hz, 1H), 7.42
(s, 1H), 7.36 (d, J = 8.6 Hz, 1H), 7.15 (d, J = 8.5 Hz, 1H), 2.35 (s, 3H), 2.32
08.1651, found: 308.1647.
(
E)-2-((2-(4-methoxyphenyl)-3-oxoprop-1-en-1-
(s, 3H), 1.92 (s, 3H); 13C NMR (150 MHz, CDCl
137.0, 136.6, 136.0, 130.0, 120.6, 115.2, 112.3, 25.2, 20.2, 9.4. ESI-MS
calcd for C13 [M+H]: 218.1181, found: 218.1176.
3
): δ 196.4, 194.8, 141.4,
1
yl)amino)benzaldehyde (3i): Yellow solid, (0.066 g, 0.23 mmol, 76%), H
NMR (600 MHz, CDCl
3
): δ 11.07 (d, J = 12.1 Hz, 1H, NH), 9.81 (s, 1H),
.46 (s, 1H), 7.66-7.58 (m, 3H), 7.37-7.34 (m, 3H), 7.13 (t, J = 7.1Hz, 1H),
.05 (d, J = 7.9 Hz, 2H), 3.84 (s, 3H); 13C NMR (150 MHz, CDCl
): δ 194.3,
89.8, 159.4, 144.2, 142.3, 136.6, 136.0, 130.5, 128.2, 123.0, 121.6, 121.2,
14.5, 112.9, 55.2, two peaks are merged. ESI-MS calcd for C17
H16NO
2
9
7
1
1
(E)-5-bromo-2-((2-methyl-3-oxobut-1-en-1-yl)amino)benzaldehyde
1
3
(4b): Yellow solid, (0.124 g, 0.44 mmol, 74%), H NMR (600 MHz, CDCl
3
):
δ 10.43 (d, J = 12.0 Hz, 1H), 9.85 (s, 1H), 7.79 (d, J = 12.5 Hz, 1H), 7.73-
7.72 (m, 1H), 7.62 (dd, J = 6.8, 2.1 Hz, 1H), 7.13 (d, J = 9.0 Hz, 1H), 2.32
H
16NO
3
[
M+H]: 282.1130, found: 282.1121.
(s, 3H), 1.93 (d, 3H); 13C NMR (150 MHz, CDCl
138.7, 138.6, 134.8, 121.8, 116.68, 114.2, 111.9, 25.4, 9.6. ESI-MS calcd
for C12 13BrNO [M+H]: 282.0130, found: 282.0128.
3
): δ 196.5, 193.5, 142.6,
(
E)-2-((2-cyclopropyl-3-oxoprop-1-en-1-yl)amino)benzaldehyde (3j):
1
Off-white solid, (0.084 g, 0.39 mmol, 75%), H NMR (600 MHz, CDCl
3
): δ
H
2
1
1.17 (d, J = 12.5 Hz, 1H, NH), 9.96 (d, J = 0.4 Hz, 1H), 9.27 (s, 1H), 7.69
(E)-5-methoxy-2-((2-methyl-3-oxobut-1-en-1-yl)amino)benzaldehyde
1
(
(
(
dd, J = 6.1, 1.6 Hz, 1H), 7.60-7.57 (m, 2H), 7.29 (d, J = 8.5 Hz, 1H), 7.13
(4c): Yellow solid, (0.109 g, 0.47 mmol, 79%), H NMR (600 MHz, CDCl
3
):
td, J = 7.4, 0.8 Hz, 1H), 1.36-1.32 (m, 1H), 1.07-1.04 (m, 2H), 0.59-0.56
δ 10.24 (d, J = 12.4 Hz, 1H), 9.89 (s, 1H), 7.84 (d, J = 12.8 Hz, 1H), 7.18
(s, 1H), 7.17 (d, J = 2.8 Hz, 1H), 7.11 (d, J = 2.8 Hz, 1H), 3.83 (s, 3H), 2.31
m, 2H); 13C NMR (150 MHz, CDCl
36.0, 121.4, 121.1, 112.6, 5.0, 4.4, two peaks are merged. ESI-MS calcd
for C13 [M+H]: 216.1025, found: 216.1032.
E)-2-((2-formyl-4-methylpenta-1,3-dien-1-yl)amino)benzaldehyde
3
): δ 194.8, 190.9, 146.3, 142.3, 136.7,
1
(s, 3H), 1.92 (d, J = 0.9 Hz, 3H); 13C NMR (150 MHz, CDCl
194.3, 153.7, 137.9, 136.3, 123.8, 120.9, 118.9, 114.8, 113.9, 55.9, 25.2,
9.4. ESI-MS calcd for C13 [M+H]: 234.1130, found: 234.1123.
(E)-3-formyl-4-((2-methyl-3-oxobut-1-en-1-yl)amino)phenyl methyl
carbonate (4d): Yellow solid, (0.128 g, 0.46 mmol, 78%), 1H NMR (600
MHz, CDCl ): δ 10.44 (d, J = 12.5 Hz, 1H), 9.88 (s, 1H), 7.83 (d, J = 12.5
3
): δ 196.3,
H14NO
2
(
(
H16NO
3
1
3
3k): Yellow liquid, (0.065 g, 0.28 mmol, 62%), H NMR (600 MHz, CDCl ):
δ 9.90 (s, 1H), 9.46 (s, 1H, NH), 9.44 (s, 1H), 7.54-7.53 (m, 1H), 7.33-7.30
m, 1H), 7.02 (d, J = 11.9 Hz, 1H), 6.82 (t, J = 7.5 Hz, 1H), 6.47 (d, J = 8.5
Hz, 1H), 6.14 (d, J = 11.9 Hz, 1H), 1.98 (s, 3H), 1.89 (s, 3H); 13C NMR (150
MHz, CDCl ): δ 194.4, 189.5, 154.4, 149.3, 147.0, 140.3, 136.9, 135.1,
34.3, 120.8, 117.4, 114.3, 27.2, 19.4. ESI-MS calcd for C14 [M+H]:
30.1181, found: 230.1176.
(
3
Hz, 1H), 7.49 (d, J = 2.8 Hz, 1H), 7.39 ( d, J = 2.8 Hz, 1H), 7.38 ( d, J = 2.8
Hz, 1H), 3.92 (s, 3H), 2.33 (s, 3H), 1.94 (s, 3H); 13C NMR (150 MHz,
3
1
2
H16NO
2
3
CDCl ): δ 196.6, 193.7, 154.2, 144.2, 141.5, 135.4, 129.2, 1278, 120.4,
6
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