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Med Chem Res (2016) 25:1260–1273
(2H, m, H-4, H-6), 6.21 (1H, q, J = 2.8 Hz, H-50), 5.17
(2H, bs, NH2), 2.33 (3H, s, COCH3), 2.03 (2H, m, CH2
CH3), 0.99 (3H, t, J = 7.5, CH2CH3). 13C NMR
(100 MHz, CD3Cl) d = 167.24 (C, C=O), 156.25 (C,
C-20), 146.62 (C, C-1), 132.37 (CH, C-5), 128.44 (CH,
C-3), 117.39 (CH, C-4), 116.18 (CH, C-6), 107.51 (C,
C-2), 91.74 (CH, C-50), 26.43 (CH2, CH2CH3), 21.56 (CH3,
COCH3), 6.70 (CH3, CH2CH3). HRESIMS m/z (pos): 234.
1242 C12H16N3O2 (calcd. 234.1243).
[2-(5-Methyl-4-propionyl-4,5-dihydro-1,3,4-oxadiazol-2-
yl)phenyl]amine (6b) Mp 124–127 °C. Yield 90 % (0.
087 g) as a light yellow solid. 1H NMR (400 MHz, CDCl3)
d = 7.61 (1H, dd, J = 1.5, 8.0 Hz, H-3), 7.23 (1H, t, J =
8.0 Hz, H-5), 6.74 (2H, m, H-4, H-6), 6.25 (1H, q, J = 5.
3 Hz, H-50), 2.63 (2H, q, J = 7.6 Hz, COCH2CH3), 1.64
(3H, d, J = 5.3 Hz, CH3), 1.19 (3H, t, J = 7.6 Hz,
COCH2CH3). 13C NMR (100 MHz, CD3Cl) d = 170.45
(C, C=O), 155.76 (C, C-20), 146.25 (C, C-1), 132.31 (CH,
C-5), 128.42 (CH, C-3), 117.20 (CH, C-4), 116.02 (CH,
C-6), 106.84 (C, C-2), 88.15 (CH, C-50), 27.18 (CH2,
COCH2CH3), 19.34 (CH3, CH3), 8.52 (CH3, COCH2CH3).
HRESIMS m/z (pos): 234.1234 C12H16N3O2 (calcd. 234.
1243).
[2-(5-Ethyl-4-propionyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)ph-
enyl]amine (6f) Mp 122–125 °C. Yield 95 % (0.097 g) as
1
a white solid. H NMR (400 MHz, CDCl3) d = 7.65 (1H,
dd, J = 1.6, 8.0 Hz, H-3), 7.27 (1H, m, H-5), 6.77 (2H, m,
H-4, H-6), 6.20 (1H, q, J = 2.8 Hz, H-50), 5.15 (2H, bs,
NH2), 2.67 (2H, m, COCH2CH3), 2.02 (2H, m, CH2CH3),
1.22 (3H, t, J = 7.6, COCH2CH3), 0.99 (3H, t, J = 7.5,
CH2CH3). 13C NMR (100 MHz, CD3Cl) d = 170.73 (C,
C=O), 156.17 (C, C-20), 146.34 (C, C-1), 132.28 (CH, C-5),
128.40 (CH, C-3), 117.15 (CH, C-4), 115.98 (CH, C-6),
106.60 (C, C-2), 91.72 (CH, C-50), 27.24 (CH2, COCH2
CH3), 26.44 (CH2, CH2CH3), 8.59 (CH3, COCH2CH3), 6.
65 (CH3, CH2CH3). HRESIMS m/z (pos): 248.1392
C13H18N3O2 (calcd. 248.1399).
[2-(4-Butyryl-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)ph-
enyl]amine (6c) Mp 132–135 °C. Yield 90 % (0.092 g)
as a light yellow solid. 1H NMR (400 MHz, CDCl3) d = 7.
60 (1H, dd, J = 1.5, 8.0 Hz, H-3), 7.24 (1H, m, H-5), 7.15
(1H, m, H-4), 6.73 (1H, m, H-6), 6.26 (1H, q, J = 5.9 Hz,
H-50), 5.26 (2H, bs, NH2), 2.59 (2H, m, COCH2CH2CH3),
1.73 (2H, m, COCH2CH2CH3), 1.63 (3H, d, J = 4.0 Hz,
CH3), 0.99 (3H, t, J = 8.0 Hz, COCH2CH2CH3). 13C
NMR (100 MHz, CD3Cl) d = 169.64 (C, C=O), 155.78
(C, C-20), 146.53 (C, C-1), 132.30 (CH, C-5), 128.41 (CH,
C-3), 117.00 (CH, C-4), 115.87 (CH, C-6), 106.59 (C,
C-2), 88.08 (CH, C-50), 35.81 (CH2, COCH2CH2CH3, 20.
09 (CH3, CH3), 17.97 (CH2,COCH2CH2CH3, 13.92 (CH3,
COCH2CH2CH3). HRESIMS m/z (pos): 248.1395
C13H18N3O2 (calcd. 248.1399).
[2-(4-Butyryl-5-ethyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)ph-
enyl]amine (6g) Mp 129–131 °C. Yield 92 % (0.099 g)
1
as a white solid. H NMR (400 MHz, CDCl3) d = 7.81
(1H, dd, J = 1.0, 6.5 Hz, H-3), 7.67 (1H, m, H-5), 7.29
(1H, m, H-4), 6.80 (1H, m, H-6), 6.26 (1H, q, J = 2.8 Hz,
H-50), 2.66 (2H, m, COCH2CH2CH3), 2.06 (2H, m, CH2
CH3), 1.82 (2H, m, COCH2CH2CH3); 1.06 (3H, t, J = 7.
4 Hz, COCH2CH2CH3), 1.02 (3H, t, J = 7.5, CH2CH3).
13C NMR (100 MHz, CD3Cl) d = 169.73 (C, C=O), 155.
61 (C, C-20), 138.27 (C, C-1), 132.82 (CH, C-5), 128.14
(CH, C-3), 122.83 (CH, C-4), 120.06 (CH, C-6), 110.58 (C,
C-2), 92.39 (CH, C-50), 36.13 (CH2, COCH2CH2CH3), 19.
18 (CH2, COCH2CH2CH3), 18.08 (CH2, CH2CH3), 13.82
(CH3, COCH2CH2CH3), 6.58 (CH3, CH2CH3). HRESIMS
m/z (pos): 262.1548 C14H20N3O2 (calcd. 262.1556).
[2-(5-Methyl-4-pentanoyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)
phenyl]amine (6d) Mp 103–105 °C. Yield 94 % (0.
1
102 g) as a white solid. H NMR (400 MHz, CDCl3) d =
7.63 (1H, dd, J = 1.1, 8.6 Hz, H-3), 7.28 (1H, dd, J = 1.6,
8.0 Hz, H-5), 7.16 (1H, m, H-4); 6.78 (1H, m, H-6), 6.33
(1H, q, J = 5.3 Hz, H-50), 2.57 (2H, m, COCH2CH2CH2
CH3), 1.73 (2H, m, COCH2CH2CH2CH3), 1.70 (3H, d,
J = 5.3 Hz, CH3), 1.44 (2H, m, COCH2CH2CH2CH3), 0.
98 (3H, t, J = 7.3 Hz, COCH2CH2CH2CH3). 13C NMR
(100 MHz, CD3Cl) d = 169.61 (C, C=O), 155.19 (C,
C-20), 138.27 (C, C-1), 132.81 (CH, C-5), 128.17 (CH,
C-3), 122.79 (CH, C-4), 120.03 (CH, C-6), 110.65 (C,
C-2), 88.83 (CH, C-50), 38.53 (CH2, COCH2CH2CH2CH3),
27.72 (CH2, COCH2CH2CH2CH3), 22.52 (CH2, COCH2
CH2CH2CH3), 20.14 (CH3, CH3), 13.85 (CH3, COCH2
[2-(5-Ethyl-4-pentanoyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)ph-
enyl]amine (6h) Mp 126–129 °C. Yield 90 % (0.103 g)
1
as a white solid. H NMR (400 MHz, CDCl3) d = 7.74
(1H, dd, J = 1.1, 8.5 Hz, H-3), 7.60 (1H, dd, J = 1.6, 7.
0 Hz, H-5), 7.51 (1H, m, H-4), 7.14 (1H, m, H-6), 6.25
(1H, q, J = 2.8 Hz, H-50), 2.68 (2H, m, COCH2CH2CH2
CH3), 2.06 (2H, m, CH2CH3), 1.76 (2H, m, COCH2CH2
CH2CH3), 1.44 (2H, m, COCH2CH2CH2CH3), 0.98 (6H,
m, COCH2CH2CH2CH3, CH2CH3). 13C NMR (100 MHz,
CD3Cl) d = 169.86 (C, C=O), 155.60 (C, C-20), 138.28 (C,
C-1), 132.82 (CH, C-5), 128.14 (CH, C-3), 122.81 (CH,
C-4), 120.05 (CH, C-6), 110.58 (C, C-2), 92.39 (CH, C-50),
CH2CH2CH3).
HRESIMS
m/z
(pos):
262.1548
C14H20N3O2 (calcd. 262.1556).
[2-(4-Acetyl-5-ethyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)phe-
nyl]amine (6e) Mp 96–97 °C. Yield 92 % (0.089 g) as a
1
light yellow solid. H NMR (400 MHz, CDCl3) d = 7.66
(1H, dd, J = 1.6, 8.0 Hz, H-3), 7.27 (1H, m, H-5), 6.80
123