18
J. Correa-Basurto et al. / European Journal of Medicinal Chemistry 42 (2007) 10e19
1
1
17.30 (C-1), 118.43 (C-4), 122.71 (C-7), 130.45 (C-6),
33.16 (C-3), 140.78 (C-9), 170.64 (C-2), 173.91 (C-8).
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8
0 0
.2.4. 2 -Oxo-2 (4-metoxyaminophenyl) butanoic acid (1q)
7
[
ꢁ
1
Yield: 90%; m.p.: 134 ꢃ 2 C; H NMR (DMSO-d ,
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6
0
3
00 MHz) d/ppm 2.74 (2H, t, J ¼ 6.2 Hz, H-2 ), 3.77 (2H, d,
0
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1
3
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6
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0
1
28.34 (C-3,5), 158.80 (C-1), 177.19 (C-4 ).
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.3. Synthesis of imides (3a, 3b and 3q)
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8
and 3q). These reactions were monitored by TLC (acetone/eth-
5 C, resulting in the corresponding N-arylimides (3a, 3b
[
anol 1:1, SiO ). The resulting mixtures were cooled and the
2
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2
[13] J. Trujillo-Ferrara, I. Va
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´
ꢁ
The solids were dried at 40 C. All syntheses were done as re-
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0 0
.3.1. N-Phenyl-pyrrolidine-1 ,4 -dione (3a)
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7
ꢁ
1
6
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d/ppm 2.30 (3H, s, H-6), 6.63 (1H, d, J ¼ 5.4 Hz, H-2), 7.12
0
0
(
2H, d, J ¼ 8.6 Hz, H-3 ,5 ), 7.34 (1H, d, J ¼ 5.4 Hz, H-3),
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0
0
13
7
7
2
1
.47 (2H, d, J ¼ 8.6 Hz, H-2 ,6 ); C NMR (DMSO-d ,
6
0
0
8
5.4 MHz) d/ppm 21.1 (C-6), 121.9 (C-3 ,5 ), 124.7 (C-
0
0
0
0
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.3.2. N-(4-Nitro-phenyl)-pyrrolidine-1 ,4 -dione (3b)
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7
ꢁ
1
Yield: 46%; m.p.: 162 C; H NMR (DMSO-d , 300 MHz)
6
[
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[
0
0
(
2H, d, J ¼ 8.6 Hz, H-3 ,5 ), 7.34 (1H, d, J ¼ 5.4 Hz, H-3),
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0
0
13
7
7
2
1
.47 (2H, d, J ¼ 8.6 Hz, H-2 ,6 ); C NMR (DMSO-d ,
6
0
0
5.4 MHz) d/ppm 21.1 (C-6), 121.9 (C-3 ,5 ), 124.7 (C-
0
0
0
0
,6 ), 130.8 (C-2), 141.1 (C-1 ), 143.3 (C-3), 148.2 (C-4 ),
50.1 (C-4), 167.0 (C-5), 169.3 (C-1).
0 0
.3.3. N-(4-Metoxy-phenyl)-pyrrolidine-1 ,4 -dione (3q)
7
ꢁ
1
Yield: 49%; m.p.: 279 C; H NMR (DMSO-d , 300 MHz)
6
d/ppm 2.30 (3H, s, H-6), 6.63 (1H, d, J ¼ 5.4 Hz, H-2), 7.12
0
0
(
2H, d, J ¼ 8.6 Hz, H-3 ,5 ), 7.34 (1H, d, J ¼ 5.4 Hz, H-3),
0
0
13
7
7
2
1
.47 (2H, d, J ¼ 8.6 Hz, H-2 ,6 ); C NMR (DMSO-d ,
6
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0
0
4.4 MHz) d/ppm 21.1 (C-6), 121.9 (C-3 ,5 ), 124.7 (C-
0
0
0
0
,6 ), 130.8 (C-2), 141.1 (C-1 ), 143.3 (C-3), 148.2 (C-4 ),
50.1 (C-4), 167.0 (C-5), 169.3 (C-1).
[
[
[
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Acknowledgements
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We are grateful to CONACyT (46168-M and ECOS M05-
S01), COFAA-SIP/IPN and Programa de Ingenier ´ı a Molecular
del IMP for scholarships and financial support to the authors.
[