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A. Ramazani et al. · Four-component Synthesis of 1,3,4-Oxadiazole Derivatives
benzyl group), 4.76 (q, 1 H, 3J = 7.0 Hz, CH), 6.94 – 7.47 6.8 Hz, CH3), 2.39 (s, 3 H, CH3), 2.48 – 2.53 and 2.71 –
(m, 11 H, arom. and vinylic). – 13C NMR (CDCl3): δ = 2.79 (2 m, 2 H, CH2CH3), 3.54 and 3.87 (AB quartet, 2 H,
18.75, 21.43 and 28.62 (4 CH3), 56.24 (C, aliphatic), 47.90 2J = 14.3 Hz, CH2 of benzyl group), 4.26 (q, 1 H, 3J =
(CH2Ph), 48.41 (CH), 109.18 and 138.44 (2 CH, vinylic), 6.8 Hz, CH), 7.24 – 7.48 (m, 11 H, arom. and vinylic). –
132.11, 140.20 and 143.80 (3 C, arom.), 126.05, 126.81, 13C NMR (CDCl3): δ = 13.75, 14.58 and 15.47 (3 CH3),
127.41, 127.94 and 129.71 (9 CH, arom.), 164.07 and 168.59 44.45 (CH2CH3), 50.80 (CH2Ph), 54.42 (CH, aliphatic),
(2 C=N). – MS: m/z = 376 (2) [M]+, 360 (6), 213 (76), 121.60 (1 CH, vinylic), 143.75 (1 C, vinylic), 132.91 and
162 (72), 145 (50), 105 (37), 91 (100), 83 (48), 69 (17), 56 134.09 (3 C, arom.), 126.07, 126.92, 127.95, 128.25, 128.50
(66), 43 (48). – C24H29N3O (375.51): calcd. C 76.76, H 7.78, and 129.54 (10 CH, arom.), 165.92 and 168.55 (2 C=N). –
N 11.19; found C 76.78, H 7.76, N 11.18.
MS: m/z = 348 (1) [M]+, 213 (44), 162 (6), 145 (9), 134
(100), 115 (12), 91 (86), 41 (10). – C22H25N3O (347.45):
calcd. C 76.05, H 7.25, N 12.09; found C 76.04, H 7.59,
N 12.08.
N-Benzyl-N-(tert-butyl)-N-(1-[5-[(E)-1-methyl-2-phenyl-1-
ethenyl]-1,3,4-oxadiazol-2-yl]ethyl)amine (5b)
Yellow oil, yield: 87 %. – IR (neat): ν = 3470, 2978, 1638,
1527, 1452, 1208, 924, 697 cm−1. – 1H NMR (CDCl3):
δ = 1.17 (s, 9 H, (CH3)3), 1.53 (d, 3 H, 3J = 7.0 Hz,
CHCH3), 2.37 (s, 3 H, CH3), 3.99 and 4.14 (AB quartet,
N-Benzyl-N-ethyl-N-(1-[5-[(E)-2-(4-methylphenyl)-1-
ethenyl]-1,3,4-oxadiazol-2-yl]ethyl)amine (5e)
Yellow oil, yield: 81 %. – IR (neat): ν = 3467, 2978, 2938,
2 H, 2J = 17.3 Hz, CH2 of benzyl group), 4.76 (q, 1 H, 1644, 1533, 1455, 971, 808 cm−1. – 1H NMR (CDCl3): δ =
3J = 7.0 Hz, CH), 7.15 – 7.45 (m, 11 H, arom. and vinylic). – 1.09 (t, 3 H, 3J = 7.0 Hz, CH3CH2), 1.57 (d, 3 H, 3J = 7.0 Hz,
13C NMR (CDCl3): δ = 14.57, 18.85 and 28.64 (5 CH3), CH3), 2.39 (s, 3 H, CH3), 2.44 – 2.55 and 2.67 – 2.78 (2 m,
56.22 (C, aliphatic), 47.95 (CH2Ph), 48.49 (CH), 121.67 2 H, CH2CH3), 3.54 and 3.87 (AB quartet, 2 H, 2J = 14.3 Hz,
(1 CH, vinylic), 143.88 (1 C, vinylic), 133.79 and 135.65 CH2 of benzyl group), 4.26 (q, 1 H, 3J = 7.0 Hz, CH), 6.99 –
(2 C, arom.), 126.01, 126.81, 127.93, 128.20, 128.48 and 7.52 (m, 11 H, arom. and vinylic). – 13C NMR (CDCl3):
129.53 (10 CH, arom.), 166.39 and 168.97 (2 C=N). – MS: δ = 13.77, 15.42 and 21.44 (3 CH3), 44.45 (CH2CH3), 50.75
m/z = 376 (2) [M]+, 360 (10), 318 (3), 270 (5), 213 (82), (CH2Ph), 54.42 (CH, aliphatic), 109.14 and 138.78 (2 CH,
199 (20), 190 (15), 162 (92), 148 (26), 105 (41), 91 (100), vinylic), 132.06, 139.86 and 140.28 (3 C, arom.), 126.93,
83 (48), 56 (43), 41 (30). – C24H29N3O (375.51): calcd. 127.44, 128.26, 128.51 and 129.72 (9 CH, arom.), 164.58
C 76.76, H 7.78, N 11.19; found C 76.77, H 7.75, N 11.20.
and 166.55 (2 C=N). – MS: m/z = 348 (1) [M]+, 227 (30),
214 (65), 185 (20), 161 (27), 134 (100), 91 (72), 69 (21),
55 (34). – C22H25N3O (347.45): calcd. C 76.05, H 7.25,
N 12.09; found C 76.02, H 7.28, N 12.10.
N-Benzyl-N-isopropyl-N-(1-[5-[(E)-1-methyl-2-phenyl-1-
ethenyl]-1,3,4-oxadiazol-2-yl]ethyl)amine (5c)
Yellow oil, yield: 84 %. – IR (neat): ν = 3459, 2970, 2956,
1528, 1454, 1173, 1105, 956 cm−1. – 1H NMR (CDCl3): δ =
N-Benzyl-N-isopropyl-N-(1-[5-[(E)-2-phenyl)-1-ethenyl]-
1,3,4-oxadiazol-2-yl]ethyl)amine (5f)
3
0.92 (d, 3 H,3J = 6.5 Hz, CH3), 1.02 (d, 3 H, J = 6.5 Hz,
3
CH3), 1.55 (d, 3 H, J = 7.0 Hz, CH3), 2.39 (s, 3 H, CH3),
Yellow oil, yield: 80 %. – IR (neat): ν = 3456, 2965,
3.15 – 3.23 (m, 1 H, CH), 3.77 and 3.90 (AB quartet, 2 H, 2929, 1649, 1525, 1385, 1173, 990, 731 cm−1. – H NMR
2J = 15.0 Hz, CH2 of benzyl group), 4.26 (q, 1 H, 3J = (CDCl3): δ = 0.90 (d, 3 H, 3J = 6.3 Hz, CH3), 1.14 (d,
7.0 Hz, CH), 7.22 – 7.45 (m, 11 H, arom. and vinylic). – 3 H, 3J = 6.3 Hz, CH3), 1.56 (d, 3 H, 3J = 6.8 Hz, CH3),
13C NMR (CDCl3): δ = 14.58, 16.96, 19.50 and 21.14 3.18 – 3.23 (m, 1 H, CH), 3.78 and 3.89 (AB quartet, 2 H,
(4 CH3), 48.30 (CH2Ph), 48.95 and 49.63 (2 CH), 121.65 2J = 15.0 Hz, CH2 of benzyl group), 4.26 (q, 1 H, 3J =
(1 CH, vinylic), 143.75 (1 C, vinylic), 133.92 and 135.75 6.8 Hz, CH), 6.99 – 7.58 (m, 12 H, arom. and vinylic). –
(2 C, arom.), 126.05, 126.75, 127.85, 128.21, 128.50 and 13C NMR (CDCl3): δ = 16.92, 19.45 and 21.23 (3 CH3),
129.55 (10 CH, arom.), 165.98 and 168.87 (2 C=N). – MS: 48.31 (CH2Ph), 48.87 and 49.63 (2 CH), 110.23 and 138.60
m/z = 360 (2) [M]+, 346 (3), 227 (7), 213 (100), 148 (90), 91 (2 CH, vinylic), 134.79 and 139.30 (2 C, arom.), 126.78,
(93), 69 (31), 56 (54), 43 (59). – C23H27N3O (361.48): calcd. 127.47, 128.23, 129 and 129.89 (10 CH, arom.), 164.49 and
1
C 76.42, H 7.53, N 11.6; found C 76.37, H 7.57, N 11.62.
167.72 (2 C=N). – C22H25N3O (347.45): calcd. C 76.05,
H 7.25, N 12.0; found C 76.07, H 7.23, N 12.11.
N-Benzyl-N-ethyl-N-(1-[5-[(E)-1-methyl-2-phenyl-1-
ethenyl]-1,3,4-oxadiazol-2-yl]ethyl)amine (5d)
N-Benzyl-N-(tert-butyl)-N-(1-[5-[(E)-2-phenyl)-1-ethenyl]-
1,3,4-oxadiazol-2-yl]ethyl)amine (5g)
Yellow oil, yield: 80 %. – IR (neat): ν = 3459, 2974, 2932,
1527, 1454, 1107, 924, 767 cm−1. – 1H NMR (CDCl3): δ =
Yellow oil, yield 81 %. – IR (neat): ν = 3467, 2977, 1647,
1
1.09 (t, 3 H, 3J = 7.0 Hz, CH3 CH2), 1.57 (d, 3 H, 3J = 1529, 1207, 970, 756 cm−1. – H NMR (CDCl3): δ = 1.17
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