7414
M. Sova et al. / Bioorg. Med. Chem. 14 (2006) 7404–7418
1566, 1509, 1457, 1372, 1307, 1128, 1008, 793, and
584 cmꢀ1 1H NMR (300 MHz, DMSO-d6): d (ppm)
(M+H)+; Anal. Calcd for C19H14O2: C, 83.19; H, 5.14.
Found: C, 83.31; H, 5.35.
;
3.86 (s, 3H, OCH3), 3.96 (s, 6H, 2· OCH3), 5.36 (s,
2H, CH2), 6.78 (s, 2H, aromatic), 7.25–7.32 (m, 2H, aro-
matic), 7.60–7.66 (m, 2H, aromatic), 8.48 (s, 1H,
CH@C); FAB MS m/z 370 (M+H)+; Anal. Calcd for
C20H18O7: C, 64.86; H, 4.86. Found: C, 64.75; H, 4.91.
4.3.9. 3,4,5-Trimethoxybenzyl 2-(benzo[d][1,3] dioxol-6-
yl)acetate (27). This compound was prepared from 2-
(benzo[d][1,3]dioxol-5-yl)acetic acid and (3,4,5-trimeth-
oxyphenyl)methanol by method B, as a colourless oil.
Yield 10%; IR (KBr): mmax 2490, 1734, 1593, 1491,
1
4.3.5. (1,3-Dioxoisoindolin-2-yl)methyl 2-oxo-2H-chro-
mene-3-carboxylate (23). This compound was prepared
from 2-oxo-2H-chromene-3-carboxylic acid and 2-
(hydroxymethyl)isoindoline-1,3-dione by method B,
and crystallized from hexane as a white solid. Yield
52%; mp 240–243 ꢁC; IR (KBr): mmax 3052, 1759, 1717,
1446, 1333, 1247, 1129, 1038, 929, and 812 cmꢀ1; H
NMR (300 MHz, CDCl3): d (ppm) 3.60 (s, 2H, CH2–
CO), 3.85 (s, 9H, 3· OCH3), 5.10 (s, 2H, O–CH2),
5.95 (s, 2H, O–CH2–O) 6.50 (s, 2H, aromatic), 6.75–
6.77 (m, 2H, aromatic), 6.82 (s, 1H, aromatic); EI MS
m/z 360 (M); Anal. Calcd for C19H20O7Æ0.75H2O: C,
61.04; H, 5.80. Found: C, 60.87; H, 5.60.
1
1612, 1563, 1409, 1301, 1243, 969, and 770 cmꢀ1; H
NMR (300 MHz, DMSO-d6): d (ppm) 6.00 (s, 2H,
CH2), 7.25–7.40 (m, 2H, aromatic), 7.55–7.72 (m, 2H,
aromatic), 7.78–7.88 (m, 2H, aromatic), 7.92–8.05 (m,
2H, aromatic), 8.53 (s, 1H, CH@C); EI MS m/z 349
(M); Anal. Calcd for C19H11NO6Æ0.25H2O: C, 64.50;
H, 3.28; N, 3.96. Found: C, 64.31; H, 3.10; N, 4.09.
4.3.10.
(1,3-Dioxoisoindolin-2-yl)methyl
2-(benzo-
[d][1,3]dioxol-6-yl)acetate (28). This compound was pre-
pared from 2-(benzo[d][1,3]dioxol-5-yl)acetic acid and
2-(hydroxymethyl)isoindoline-1,3-dione by method B,
and crystallized from ethyl acetate as a white solid. Yield
40%; mp 126–129 ꢁC; IR (KBr): mmax 3483, 2914, 1784,
4.3.6. 2-(1,3-Dioxoisoindolin-2-yl)ethyl 2-oxo-2H-chro-
mene-3-carboxylate (24). This compound was prepared
from 2-oxo-2H-chromene-3-carboxylic acid and 2-(2-
hydroxyethyl)isoindoline-1,3-dione by method B, as a
white solid. Yield 10%; mp 193–196 ꢁC; IR (KBr): mmax
3082, 2961, 1763, 1714, 1608, 1567, 1427, 1245, 1017,
1715, 1492, 1405, 1240, 1131, 978, 800, and 724 cmꢀ1
;
1H NMR (300 MHz, CDCl3): d (ppm) 3.55 (s, 2H,
CH2–CO), 5.75 (s, 2H, CH2–N), 5.95 (s, 2H, O–CH2–
O), 6.67–6.80 (m, 3H, aromatic), 7.76–7.84 (m, 2H, aro-
matic), 7.90–7.98 (m, 2H, aromatic); EI MS m/z 339
(M); Anal. Calcd for C18H13NO6: C, 63.70; H, 3.83;
N, 4.13. Found: C, 63.35; H, 3.98; N, 4.38.
1
and 722 cmꢀ1; H NMR (300 MHz, CDCl3): d (ppm)
4.10 (t, J = 5.3 Hz, 2H, CH2N), 4.60 (t, J = 5.3 Hz,
2H, OCH2), 7.31–7.38 (m, 2H, aromatic), 7.61–7.67
(m, 2H, aromatic), 7.71–7.76 (m, 2H, aromatic), 7.84–
7.89 (m, 2H, aromatic), 8.55 (s, 1H, CH@C); EI MS
m/z 363 (M); Anal. Calcd for C20H13NO6: C, 66.10; H,
3.58; N, 3.86. Found: C, 66.46; H, 3.29; N, 3.70.
4.3.11. (E)-Benzyl cinnamate (29). This compound was
prepared from trans-cinnamic acid and benzyl alcohol
by method A, as white crystals. Yield 79%; mp 33–
35 ꢁC, (lit.37 mp 33–33.5 ꢁC); IR (KBr): mmax 3029
1709, 1638, 1495, 1450, 1372, 1312, 1161, 981, 905,
1
755, 697, and 527 cmꢀ1; H NMR (300 MHz, CDCl3):
4.3.7. (E)-2-(1,3-Dioxoisoindolin-2-yl) ethyl cinnamate
(25). This compound was prepared from trans-cinnamic
acid and 2-(2-hydroxyethyl) isoindoline-1,3-dione by
method A, as a white solid. Yield 45%; mp 115–
118 ꢁC; IR (KBr): mmax 2929, 2119, 1777, 1708, 1627,
1428, 1392, 1320, 1255, 1202, 1067, 1016, 866, and
d (ppm) 5.32 (s, 2H, CH2), 6.55 (d, J = 16.0 Hz, 1H,
CH@CH–CO), 7.35–7.51 (m, 8H, aromatic), 7.52–7.60
(m, 2H, aromatic), 7.80 (d, J = 16.0 Hz, 1H, CH@CH–
CO); FAB MS m/z 239 (M+H)+.
4.3.12. (E)-Phenyl cinnamate (30). This compound was
prepared from trans-cinnamic acid and phenol by meth-
od A, as slightly yellow crystals. Yield 75%; mp 72–
75 ꢁC, (lit.38 mp 73.5–75.5 ꢁC); IR (KBr): mmax 3435,
2117, 1726, 1639, 1484, 1450, 1307, 1206, 1146, 970,
1
723 cmꢀ1 ; H NMR (300 MHz, CDCl3): d (ppm) 4.07
(t, J = 5.3 Hz, 2H, CH2), 4.47 (t, J = 5.3 Hz, 2H,
CH2), 6.39 (d, J = 15.8 Hz, 1H, CH@CH–CO), 7.34–
7.43 (m, 3H, aromatic), 7.47–7.57 (m, 2H, aromatic),
7.68 (d, J = 15.8 Hz, 1H, CH@CH–CO), 7.72–7.78 (m,
2H, aromatic), 7.84–7.93 (m, 2H, aromatic); FAB MS
m/z 322 (M+H)+; Anal. Calcd for C19H15NO4Æ0.25H2O:
C, 70.04; H, 4.79; N, 4.30. Found: C, 70.20; H, 5.25; N,
4.59.
1
762, 680, and 552 cmꢀ1; H NMR (300 MHz, CDCl3):
d (ppm) 6.67 (d, J = 16.0 Hz, 1H, CH@CH–CO), 7.17–
7.32 (m, 3H, aromatic), 7.39–7.51 (m, 5H, aromatic),
7.58–7.66 (m, 2H, aromatic), 7.90 (d, J = 16.0 Hz, 1H,
CH@CH–CO); FAB MS m/z 225 (M+H)+.
4.3.8. (E)-1-Naphthyl cinnamate (26). This compound
was prepared from trans-cinnamic acid and 1-naphthol
by method A, as a brown solid. Yield 20%; mp 105–
108 ꢁC; IR (KBr): mmax 3042, 1723, 1629, 1449, 1310,
4.3.13. (E)-3-Phenoxyphenyl cinnamate (31). This com-
pound was prepared from trans-cinnamic acid and (3-
phenoxyphenyl)methanol by method B, as white crys-
tals. Yield 84%; mp 48–51 ꢁC; IR (KBr): mmax 3038,
2942, 1713, 1638, 1583, 1484, 1450, 1378, 1312, 1250,
1134, 1014, 865, 767, and 684 cmꢀ1
;
1H NMR
(300 MHz, CDCl3): d (ppm) 6.84 (d, J = 16.0 Hz, 1H,
CH@CH–CO), 7.34–7.39 (m, 1H, aromatic), 7.44–7.51
(m, 3H, aromatic), 7.51–7.58 (m, 3H, aromatic), 7.63–
7.71 (m, 2H, aromatic), 7.79 (d, J = 8.3 Hz, 1H, aromat-
ic), 7.88–7.99 (m, 2H, aromatic), 7.99–8.06 (d,
J = 16.0 Hz, 1H, CH@CH–CO); FAB MS m/z 275
1218, 1166, 1074, 982, 804, 749, and 686 cmꢀ1 1H
;
NMR (300 MHz, CDCl3): d (ppm) 5.53 (s, 2H, CH2),
6.52 (d, J = 16.0 Hz, 1H, CH@CH–CO), 6.96–7.21
(m, 6H, aromatic), 7.31–7.46 (m, 6H, aromatic),
7.50–7.60 (m, 2H, aromatic), 7.76 (d, J = 16.0 Hz,
1H, CH@CH–CO); FAB MS m/z 331 (M+H)+; Anal.