Arkivoc 2017, iii, 151-165
Chernyshova, N. B. et al.
(
2E)-3-(4-Methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (3aa). Bright yellow crystals; Yield 5.12
38
1
g, 78%; mp 99–101 C (Lit. 100–101 C); H NMR (DMSO-d
6
): δ 7.88 (2H, d, J 8.8 Hz, H-2'',6''), 7.81 (1H, d, J
1
5.5 Hz, H-2), 7.72 (1H, d, J 15.5 Hz, H-3), 7.42 (2H, s, H-2',6'), 7.03 (2H, d, J 8.8 Hz, H-3'',5''), 3.90 (6H, s, OCH -
3
+
+
3',5'), 3.83 (3H, s, OCH
3
), 3.77 (3H, s, OCH ); EIMS m/z 329 [M+1] (19), 328 [M] (100), 327 (13), 314 (12), 313
3
(
59), 297 (29), 285 (20), 195 (31), 171 (12), 161 (65), 133 (44), 118 (22), 109 (14), 89 (27), 77 (35); Anal. Calcd.
: C, 69.50; H, 6.14. Found: C, 69.62; H, 6.18.
2E)-3-(3-Hydroxy-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (3ab). Yellow crystals; Yield
for C19
(
4
2
6
H O
20 5
3
9
1
.2 g, 61%; mp 126–128 C (Lit. 127–129 C); H NMR (DMSO-d
), 7.62 (1H, d, J 15.4 Hz, H-3), 7.40 (2H, s, H-2',6'), 7.39 (1H, d, J 2 Hz, H-2''), 7.30 (1H, dd, J 8.3 Hz, J 2 Hz, H-
''), 7.00 (1H, d, J 8.3 Hz, 5''), 3.90 (6H, s, OCH -3',5'), 3.84 (3H, s, OCH ), 3.76 (3H, s, OCH ); EIMS m/z 345
6
): δ 9.19 (1H, s, OH), 7.71 (1H, d, J 15.4 Hz, H-
3
3
3
+
+
[M+1] (21), 344 [M] (100), 330 (12), 329 (58), 313 (25), 301 (17), 195 (37), 177 (34), 156 (24), 134 (18), 117
(17), 106 (10), 105 (13), 89 (28), 77 (26); Anal. Calcd. for C19 : C, 66.27; H 5.85. Found: C, 66.40; H, 5.88.
(2E)-3-(3-Hydroxy-4-methoxyphenyl)-1-(4-methoxyphenyl)-2-propen-1-one (3bb). The reaction mixture was
H O
20 6
40
1
stirred at room temperature for 72 h. Yellow crystals; Yield 3.18 g, 56%; mp 149–151 C (Lit. 150–152 C); H
NMR (DMSO-d ): δ 9.10 (1H, s, OH), 8.13 (2H, d, J 8.7 Hz, H-2',6'), 7.69 (1H, d, J 15.5 Hz, H-2), 7.59 (1H, d, J 15.5
Hz, H-3), 7.31 (1H, s, H-2''), 7.28 (1H, d, J 8.3 Hz, H-6''), 7.07 (2H, d, J 8.7 Hz, H-3',5'), 7.0 (1H, d, J 8.3 Hz, 5''),
3
1
5
6
+
+
.87 (3H, s, OCH
3
), 3.84 (3H, s, OCH ); EIMS m/z 285 [M+1] (10), 284 [M] (51), 283 (16), 269 (32), 241 (10),
3
77 (11), 135 (83), 117 (14), 107 (27), 105 (20), 92 (71), 89 (41), 77 (100); Anal. Calcd. for C17
H
16
O : C, 71.82; H,
4
.67. Found: C, 71.88; H, 5.70.
(
2E)-1-(3-Hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one (3ca). Acetyl group was
hydrolyzed during the condensation of 5-acetyl-2-methoxyphenyl acetate (1c) and anisaldehyde (2a) (Scheme
1
3
). Yellow crystals; Yield 3.24 g, 57%; mp 106–108 C; H NMR (DMSO-d
6
): δ 9.35 (1H, s, OH), 7.82 (2H, d, J 8.7
Hz, H-2'',6''), 7.74 (1H, d, J 15.5 Hz, H-2), 7.73 (1H, dd, J 8.5 Hz, J 2.0 Hz, H-6'), 7.65 (1H, d, J 15.5 Hz, H-3), 7.52
(
1H, d, J 2.0 Hz, H-2'), 7.05 (1H, d, J 8.5 Hz, H-5'), 7.01 (2H, d, J 8.5 Hz, H-3'',5''), 3.88 (3H, s, OCH
3
), 3.82 (3H, s,
); EIMS m/z 285 [M+1] (19), 284 [M] (100), 283 (23), 269 (53), 253 (20), 161 (46), 151 (37), 133 (25), 108
: C, 71.82; H, 5.67. Found: C, 71.96; H, 5.72%.
2E)-1-(4-Methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one (3d). Yellow crystals; Yield 4.86 g,
+
+
OCH
3
(19), 89 (24), 77 (25); Anal. Calcd. for C17
H O
16 4
(
36
1
7
4%; mp 132–134 C (Lit. 131–133 C); H NMR (DMSO-d
6
): δ 8.18 (2H, d, J 8.9 Hz, H-2',6'), 7.89 (1H, d, J 15.5
),
); EIMS m/z 329 [M+1] (19), 328 [M] (84), 327 (13), 314 (6), 313
30), 298 (8), 297 (40), 285 (18), 225 (10), 171 (15), 135 (86), 133 (10), 128 (14), 120 (11), 119 (10), 107 (30), 77
100); Anal. Calcd. for C, 69.50; H, 6.14. Found: C19 , C, 69.59; H, 6.17.
2E)-1-(3-Hydroxy-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one (3e). Acetyl group was
Hz, H-2), 7.66 (1H, d, J 15.5 Hz, H-3), 7.22 (2H, s, H-2'',6''), 7.10 (2H, d, J 8.9 Hz, H-3',5'), 3.88 (3H, s, OCH
3
(
(
(
3
+
+
.87 (6H, s, OCH
3
-3'',5''), 3.72 (3H, s, OCH
3
H O
20 5
hydrolyzed during the condensation of 5-acetyl-2-methoxyphenyl acetate (1c) and 3,4,5-
39
1
trimethoxybenzaldehyde. Yellow crystals;Yield 4.34 g, 63%; mp 129–131 C (Lit. 130–132 C); H NMR
DMSO-d ): δ 9.39 (1H, s, OH), 7.83 (1H, d, J 15.5 Hz, H-2), 7.76 (1H, dd, J 8.5 Hz, J 1.8 Hz, H-6'), 7.62 (1H, d, J
5.4 Hz, H-3), 7.54 (1H, d, J 1.8 Hz, H-2'), 7.20 (2H, s, H-2'',6''), 7.07 (1H, d, J 8.5 Hz, 5'), 3.88 (3H, s, OCH ), 3.87
); EIMS m/z 345 [M+1] (19), 344 [M] (100), 330 (8), 329 (40), 314 (9),
13 (42), 301 (13), 157 (5), 151 (13), 127 (6); Anal. Calcd. for C19 : C, 66.27; H, 5.85. Found: C, 66.37; H,
.89.
(
6
1
3
+
+
(6H, s, OCH
3
-3'',5''), 3.71 (3H, s, OCH
3
3
5
H O
20 6
General procedure for the synthesis of chalcone acetates 3ab-Ac, 3bb-Ac, and 3ca-Ac. The mixture of AcCl
(1.18 g, 15 mmol) and pyridine (1.19 g, 15 mmol) in abs. CH
2
Cl
2
(15 mL) was added by small portions to a
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