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3-[3-(o-Tolyl)-1,2,4-oxadiazol-5-yl]propionamide (4b): IR: ν 3436 (N-H, asymm.), 3250 (N-H,
1
Symm), 1695 (C=O) cm-1; H-NMR (CDCl3): δ 2.61 (s, 3H, CH3), 2.86 (t, 2H, J = 7.2Hz, CH2-7),
3.31 (t, 2H, J = 7.2 Hz, CH2-6), 5.55 and 5.70 (2bs, 2H, NH2), 7.29-7.41 (m, 3H, arom.), 7.94 (d, 1H,
J= 9.3Hz, arom.); Anal. calcd. for C12H13O2N3: C, 62.33, H, 5.67, N, 18.17. Found: C, 62.22, H, 5.93,
N, 18.56.
3-[3-(m-Tolyl)-1,2,4-oxadiazol-5-yl]propionamide (4c): IR: ν 3347 (N-H, asymm.), 3250 (N-H,
1
symm.), 1694 (C=O) cm-1; H-NMR (CDCl3): δ 2.42 (s, 3H, CH3), 2.85 (t, 2H, J = 7.2 Hz, CH2-7),
3.30 (t, 2H, J = 7.2 Hz, CH2-6), 5,71 and 5,78 (2bs, 2H, NH2), 7.26 -7.39 (m, 2H, arom.), 7.80-8.00 (m,
2H, arom.); Anal. calcd. for C12H13O2N3: C, 62.33, H, 5.67, N, 18.17. Found: C, 62.40, H, 5.71, N,
17.98.
3-[3-(p-Tolyl)-1,2,4-oxadiazol-5-y]propionamide (4d): IR: ν 3323 (N-H, asymm.), 3250 (N-H, symm.),
1
1693 (C=O) cm-1; H-NMR (CDCl3): δ 2.41 (s, 3H, CH3 ), 2.85 (t, 2H, J = 7.2 Hz, CH2-7), 3.29 (t, 2H,
J = 7.2 Hz, CH2-6), 5.46 and 5.70 (2bs, 2H, NH2), 7.28 (d, 2H, J = 7.2 Hz, H-3' & H-5'), 7.93 (d, 2H, J
= 7.2 Hz, H-2' & H-6'); Anal. calcd. for C12H13O2N3: C, 62.33, H, 5.67, N, 18.17. Found: C, 62.36, H,
5.69, N, 18.20.
3-[3-(4-Anisyl)-1,2,4-oxadiazol-5-yl]propionamide (4e): IR: ν 3339 (N-H, asymm.), 3250 (N-H,
1
symm.), 1693 (C=O) cm-1; H-NMR (CDCl3)\: δ 2.85 (t, 2H, J = 7.2 Hz, CH2-7), 3.29 (t, 2H, J = 7.2
Hz, CH2-6), 3.87 (s, 3H, CH3O-), 5.39 and 5.69 (2bs, 2H, NH2), 6.78 (d, 2H, J = 9.0 Hz, H-3' & H-5',
arom.), 7.99 (d, 2H, J = 9.0 Hz, H-2' & H-6', arom.); Anal. calcd for C12H13O3N3: C, 58.29, H, 5.30, N,
16.99. Found: C, 58.61, H, 5.41, N, 17.01.
3-[3-(4-Bromophenyl)-1,2,4-oxadiazol-5-yl]propionamide (4f): IR: ν 3350 (N-H, asymm.), 3250 (N-H,
1
symm.), 1669 (C=O) cm-1; H-NMR (DMSO-d6): δ 2.68 (t, 2H, J = 7.2 Hz, CH2-7), 3.16 (t, 2H, J =
7.2 Hz, CH2-6), 6.85 and 7.49 (2bs, 2H, NH2), 7.77 (d, 2H, J = 8.4 Hz, H-3' & H-5', arom.), 7.92 (d,
2H, J = 8.4 Hz, H-2' & H-6', arom.); Anal. calcd. for C11H10O2N3Br: C, 44.62, H, 3.40, N, 14.19.
Found: C, 44.81, H, 3.68, N, 14.00.
References and Notes
1. Clapp, L.B. In “Advances in Heterocyclic Chemistry”; Katritzky, A.R., Ed.; Academic Press: New
York, 1976; 20, pp. 65-116.
2. Clapp, L.B. In “Comprehensive Heterocyclic Chemistry”; Katritzky, A.R.; Rees, C.W., Eds.;
Pergamon Press: Oxford, 1984, 6, pp. 365-391.
3. Jochims, J.C. In “Comprehensive Heterocyclic Chemistry II”; Katritzky, A.R.; Rees, C.W.;
Scriven, E.F.D., Eds.; Elsevier Science: Oxford, 1996; 4, pp. 179-228.
4. Hemming, K. Recent developments in the synthesis, chemistry and applications of the fully
unsaturated 1,2,4- oxadiazoles. J. Chem. Res. 2001, 216, 209-216.
5. Antunes, R.; Batista, H.; Srivastava, R.M.; Thomas, G.; Araújo, C.C.; Longo, R.L.; Magalhães, H.;
Leão, M.B.C.; Pavão, A.C. Synthesis, characterization and interaction mechanism of new
oxadiazolo-phthalimides as peripheral analgesics. IV. J. Mol. Struct. 2003, 600, 1-13.