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into a fine powder. It was filtered off, repeatedly washed on the filter with anhydrous ethyl ether and
allowed to dry in a vacuum oven for 8 hours at 40-45ºC. Finally it was purified by recrystallization
from anhydrous dioxane.
2-(meta-Formylaminophenyl)-4-(β-carboxymethyl)-Δ2-oxazolin-5-one (10). Yellow solid; yield 67 %
(351 mg); m.p. 180-182ºC. Anal. Calc. for C12H10N2O5: 54.97 % C, 3.84 % H, 10.68 % N; Found:
54.08 % C, 4.24 % H, 10.12 % N; IR (ν, cm-1): 3320, 3520 (NH); 1775, 1800 (CO); 1080 (C-O-C);
1
1620 (C=N); 710 (CH); H-NMR δ (CD3CN, 300 MHz): 2.90-3.00 (m, 2H, CH2); 4.95 (t, 1H, CH);
6.60 (s, 1H, NH); 7.65 (t, 1H, Ar); 7.95 (d, 2H, Ar); 8.20 (s, 1H, Ar).
2-(meta-Formylaminophenyl)-4-(β-amidomethyl)-Δ2-oxazolin-5-one (11). Yellow solid; yield 69 %
(360 mg); m.p. 198-200ºC. Anal. Calc. for C12H10N3O4: 55.17 % C, 4.24 % H, 16.09 % N; Found:
55.41 % C, 4.54 % H, 16.61 % N; IR (ν, cm-1): 3325, 3500 (NH); 1760, 1795 (CO); 1088 (C-O-C);
1625 (C=N); 715 (CH); 1H-NMR δ (DMSO-d6, 300 MHz): 2.90-3.00 (m, 2H, CH2); 5.00 (t, 1H, CH);
6.60 (s, 2H, NH2); 7.70 (t, 1H, Ar); 7.95 (d, 2H, Ar); 8.20 (s, 1H, Ar).
2-(meta-Formylaminophenyl)-4-(β-methylthioethyl)-Δ2-oxazolin-5-one (12). Yellow solid; yield 62.2
% (345 mg); m.p. 182-183ºC. Anal. Calc. for C13H14N2O3S: 56.11 % C, 5.03 % H, 10.07 % N, 11.51
% S; Found: 55.83 % C, 4.87 % H, 10.01 % N, 11.32 % S; IR (ν, cm-1): 3429 (NH); 1751, 1631 (CO);
1
1610 (C=N); 1155 (C-O-C); 835 (CH); 654 (C-S); H-NMR δ (DMSO-d6, 300 MHz): 2.08 (s, 3H,
CH3); 2.50 (m, 4H, CH2); 4.57 (t, 1H, CH); 6.22 (d, 1H, NH); 7.80 (t, 1H, Ar); 8.32 (d, 2H, Ar); 8.39
(d, 1H, Ar); 8.74 (s, 1H, Ar); 9.70 (d, 1H, CH).
2-(meta-Acetylaminophenyl)-4-(β-carboxymethyl)-Δ2-oxazolin-5-one (13). Yellow solid; yield 63.8 %
(352 mg); m.p. 149-150ºC. Anal. Calc. for C13H12N2O5: 56.52 % C, 4.38 % H, 10.14 % N; Found:
56.98 % C, 4.74 % H, 10.62 % N; IR (ν, cm-1): 3084, 3210 (NH); 1730, 1770 (CO); 1084 (C-O-C);
1620 (C=N); 728 (CH); 1H-NMR δ (CD3CN, 300 MHz): 2.95 (d, 2H, CH2); 4.50 (s, 3H, CH3); 5.20 (t,
1H, CH); 6.50 (s, 2H, NH); 7.70 (t, 1H, Ar); 8.00 (d, 2H, Ar); 8.25 (s, 1H, Ar).
2-(meta-Acetylaminophenyl)-4-(β-amidoethyl)-Δ2-oxazolin-5-one (14). White solid; yield 61.5 % (337
mg); m.p. 168-170ºC. Anal. Calc. for C13H13N3O4: 56.72 % C, 4.76 % H, 15.27 % N; Found: 56.91 %
C, 4.95 % H, 15.43 % N; IR (ν, cm-1): 3100, 3320 (NH); 1770, 1800 (CO); 1084 (C-O-C); 1620
1
(C=N); 705 (CH); H-NMR δ (DMSO-d6, 300 MHz): 2.80 (d, 2H, CH2); 4.50 (s, 3H, CH3); 5.05 (t,
1H, CH); 5.70 (s, 1H, NH); 6.60 (s, 2H, NH2); 7.70 (t, 1H, Ar); 7.90 (d, 2H, Ar); 8.20 (s, 1H, Ar).
2-(meta-Acetylaminophenyl)-4-(β-methylthioethyl)-Δ2-oxazolin-5-one (15). Brown solid; yield 58.7 %
(342 mg); m.p. 142-143ºC. Anal. Calc. for C14H16N2O3S: 57.53 % C, 5.47 % H, 9.58 % N, 10.95 % S;
Found: 57.18 % C, 5.21 % H, 9.24 % N, 10.81 % S; IR (ν, cm-1): 3080, 3240 (NH); 1680, 1815 (CO);
1
1078 (C-O-C); 1615 (C=N); 820 (CH); 725 (C-S); H-NMR δ (DMSO-d6, 400 MHz): 2.07 (s, 3H,
CH3); 2.26 (s, 3H, CH3); 2.57 (m, 4H, CH2); 4.57 (m, 1H, CH); 5.73 (s, 1H, NH); 7.80 (t, 1H, Ar); 8.33
(d, 1H, Ar); 8.39 (d, 1H, Ar); 8.74 (s, 1H, Ar).