4
M. Ouattara et al. / C. R. Chimie xxx (2016) 1e7
Tableau 1
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Donnees physicochimiques des groupements caracteristiques des composes 5aey.
CH3
N
R
N
O
Donnees physicochimiques : 1H, 13C NMR (DMSO-d6,
d ppm) de eC]N, CH3, eCOeCH]CHeet donnees ESI masse
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Composes R
5a
5b
5c
5d
5e
5f
H
1H: 7.80 (1H, d, J ¼ 15.6 Hz, CH]CH); 7.50 (1H, d, J ¼ 15.6 Hz, CH]CH); 2.89 (3H, s, CH3). 13C: 179.50 CO); 151.98 CN), 141.56 (CH]
CH); 121.69 (CH]CH); 18.36 (CH3). ESþ SM: 263 [MþHþ]. Recristallisation : MeCN/H2O (1:1). Rendement : 80%. PF: 156e158 ꢀ
C
2-CH3
3-CH3
4-CH3
4-
1H: 7.75 (1H, d, J ¼ 16 Hz, CH]CH); 7.48 (1H, d, J ¼ 16 Hz, CH]CH); 2.89 (3H, s, CH3). 13C: 179.35 CO); 152.04 CN); 141.50 (CH]
CH); 121.70 (CH]CH); 18.12 (CH3). ESþ SM: 277 [MþHþ]. Recristallisation : cyclohexane. Rendement : 70%. PF: 153e155 ꢀC
1H: 7.75 (1H, d, J ¼ 16 Hz, CH]CH); 7.54 (1H, d, J ¼ 16 Hz, CH]CH); 2.81 (3H, s, CH3). 13C: 179.22 CO); 152.07 CN); 141.57 (CH]
CH); 121.77 (CH]CH); 18.09 (CH3). ESþ SM: 277 [MþHþ]. Recristallisation : hexane/DCM (3:1). Rendement : 71%. PF: 127e130 ꢀ
C
1H: 7.75 (1H, d, J ¼ 16 Hz, CH]CH); 7.48 (1H, d, J ¼ 16 Hz, CH]CH); 2.89 (3H, s, CH3). 13C: 179.36 CO); 151.98 CN); 141.56 (CH]
CH); 121.70 (CH]CH); 18.10 (CH3). ESþ SM: 277 [MþHþ]. Recristallisation : cyclohexane. Rendement : 68%. PF: 151e153 ꢀC
1H: 7.78 (1H, d, J ¼ 15.8 Hz, CH]CH); 7.45 (1H, d, J ¼ 15.8 Hz, CH]CH); 2.89 (3H, s, CH3). 13C: 179.36 CO); 151.98 CN);; 141.56
CH(CH3)2 (CH]CH); 121.70 (CH]CH); 18.10 (CH3). ESþ SM: 305 [MþHþ]. Recristallisation : hexane. Rendement : 58%. PF: 132e135 ꢀC
2-OH
1H: 7.80 (1H, d, J ¼ 15.6 Hz, CH]CH); 7.38 (1H, d, J ¼ 15.6 Hz, CH]CH); 2.78 (3H, s, CH3). 13C: 179.50 CO); 151.95 CN); 141.56
þ
(CH]CH); 120.89 (CH]CH); 18.26 (CH3). ESþ SM: 279 [MþH ]. Recristallisation : ethanol. Rendement : 56%. PF: > 260 ꢀC
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5g
5h
5i
3-OH
1H: 7.80 (1H, d, J ¼ 15.6 Hz, CH]CH); 7.38 (1H, d, J ¼ 15.6 Hz, CH]CH); 2.78 (3H, s, CH3). 13C: 179.17 CO); 152.01 CN); 141.59
þ
(CH]CH); 120.70 (CH]CH); 18.07 (CH3). ESþ SM: 279 [MþH ]. Recristallisation : ethanol. Rendement : 70%. PF: 255e257 ꢀC
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4-OH
1H: 7.80 (1H, d, J ¼ 15.6 Hz, CH]CH); 7.38 (1H, d, J ¼ 15.6 Hz, CH]CH); 2.78 (3H, s, CH3). 13C: 179.39 CO); 151.43 CN); 141.97
þ
(CH]CH); 121.88 (CH]CH); 18.10 (CH3). ESþ SM: 279 [MþH ]. Recristallisation : ethanol. Rendement : 57%. PF: > 260 ꢀC
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2-OCH3
1H: 7.72 (1H, d, J ¼ 15.6 Hz, CH]CH); 7.50 (1H, d, J ¼ 15.6 Hz, CH]CH); 2.80 (3H, s, CH3). 13C: 179.30 CO); 152.05 CN); 141.22
(CH]CH); 120.90 (CH]CH); 18.20 (CH3). ESþ SM: 293 [MþHþ]. Recristallisation : hexane/DCM (3:1). Rendement : 71%. PF: 196
e198 ꢀC
5j
3-OCH3
4-OCH3
1H: 7.72 (1H, d, J ¼ 15.6 Hz, CH]CH); 7.50 (1H, d, J ¼ 15.6 Hz, CH]CH); 2.80 (3H, s, CH3). 13C: 179.30 CO); 152.05 CN); 141.22
(CH]CH); 120.92 (CH]CH); 18.03 (CH3). ESþ SM: 293 [MþHþ]. Recristallisation : hexane/DCM (3:1). Rendement : 70%. PF: 127
e129 ꢀC
5k
5l
1H: 7.72 (1H, d, J ¼ 15.6 Hz, CH]CH); 7.48 (1H, d, J ¼ 15.6 Hz, CH]CH); 2.79 (3H, s, CH3). 13C: 179.41 (C]O); 151.70 (C]N);
141.52 (CH]CH); 121.89 (CH]CH); 18.11 (CH3). ESþ SM: 293 [MþH ]. Recristallisation : acetate d’ethyle. Rendement : 73%. PF:
þ
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158e160 ꢀC
3,4-di-
OCH3
1H: 7.66 (1H, d, J ¼ 15.6 Hz, CH]CH); 7.33 (1H, d, J ¼ 15.4 Hz, CH]CH); 2.81 (3H, s, CH3). 13C: 179.45 (C]O); 148.90 (C]N);
141.92 (CH]CH); 121.89 (CH]CH); 18.0 (CH3). ESþ SM: 323 [MþHþ]. Recristallisation : hexane/DCM (3:1). Rendement : 70%. PF:
169e171 ꢀC
5m
2,5-di-
OCH3
1H: 7.66 (1H, d, J ¼ 15.6 Hz, CH]CH); 7.35 (1H, d, J ¼ 15.4 Hz, CH]CH); 2.80 (3H, s, CH3). 13C: 179.60 (C]O); 146.49 (C]N);
141.92 (CH¼CH); 121.89 (CH]CH); 18.16 (CH3). ESþ SM: 323 [MþHþ]. Recristallisation : hexane/DCM (3:1). Rendement : 86%. PF:
165e167 ꢀC
5n
5o
4-
1H: 7.78 (1H, d,J¼ 16 Hz, CH]CH); 7.45 (1H, d,J¼ 16 Hz, CH]CH); 2.85 (3H, s, CH3). 13C: 179.36 (C]O); 151.98 (C]N); 141.46
N(CH3)2 (CH]CH); 121.70 (CH]CH); 18.10 (CH3). ES þ SM: 306 [MþHþ]. Recristallisation : eau. Rendement : 30%. PF: 197e200 ꢀC.
2-Cl
3-Cl
4-Cl
1H: 7.80 (1H, d, J ¼ 15.6 Hz, CH]CH); 7.43 (1H, d, J ¼ 15.9 Hz, CH]CH); 2.83 (3H, s, CH3). 13C: 179.20 (C]O); 152.68 (C]N);
139.90 (CH]CH); 120.89 (CH]CH); 18.16 (CH3). ESþ SM: 297.75 [MþHþ]. Recristallisation : hexane/DCM (3:1). Rendement : 65%.
PF: 170e172 ꢀC
5p
5q
5r
1H: 7.88 (1H, d, J ¼ 15.6 Hz, CH]CH); 7.55 (1H, d, J ¼ 15.9 Hz, CH]CH); 2.82 (3H, s, CH3). 13C: 179.15 (C]O); 152.62 (C]N);
139.85 (CH]CH); 120.89 (CH]CH); 18.16 (CH3). ESþ SM: 297.75 [MþHþ]. Recristallisation : hexane/DCM (3:1). Rendement : 82%.
PF: 167e169 ꢀC
1H: 7.80 (1H, d, J ¼ 15.6 Hz, CH]CH); 7.51 (1H, d, J ¼ 15.9 Hz, CH]CH); 2.79 (3H, s, CH3). 13C: 180.0 (C]O); 152.62 (C]N); 139.85
(CH]CH); 120.89 (CH]CH); 18.10 (CH3). ESþ SM: 297.75 [MþHþ].Recristallisation : hexane/DCM (3:1). Rendement : 72%. PF: 173
e175 ꢀC
2,6-di-Cl 1H: 7.86 (1H, d, J ¼ 16 Hz, CH]CH); 7.54 (1H, d, J ¼ 16 Hz, CH]CH); 2.79 (3H, s, CH3). 13C: 179.29 (C]O); 152.78 (C]N); 139.91
þ
(CH]CH); 120.89 (CH]CH); 18.16 (CH3). ESþ SM: 332 [MþH ]. Recristallisation : acetate d’ethyle. Rendement : 55%. PF: 180
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e182 ꢀC
5s
2,4-di-Cl 1H: 7.86 (1H, d,J¼ 16 Hz, CH]CH); 7.54 (1H, d,J¼ 16 Hz, CH]CH); 2.76 (3H, s, CH3). 13C: 179.29 (C]O); 152.78 (C]N); 139.91
(CH]CH); 120.89 (CH]CH); 18.16 (CH3). ES þ SM: 332 [MþHþ]. Recristallisation : hexane/DCM (3:1). Rendement : 90%. PF: 197
e199 ꢀC
5t
2-Br
3-Br
4-Br
4-F
1H: 8.15 (1H, d, J ¼ 15.3 Hz, CH]CH); 7.90 (1H, d, J ¼ 15.3 Hz, CH]CH); 3.04 (3H, s, CH3). 13C: 178.53 (C]O); 152.67 (C]N);
138.81 (CH]CH); 120.89 (CH]CH); 18.14 (CH3). ESþ SM: 342 [MþHþ]. Recristallisation : hexane/DCM (3:1). Rendement : 85%. PF:
178e180 ꢀC
5u
5v
5w
1H: 7.75 (1H, d, J ¼ 15.3 Hz, CH]CH); 7.60 (1H, d, J ¼ 15.3 Hz, CH]CH); 2.88 (3H, s, CH3). 13C: 179.13 (C]O); 152.62 (C]N);
139.80 (CH]CH); 121.85 (CH]CH); 18.13 (CH3). ESþ SM: 342 [MþHþ]. Recristallisation : hexane/DCM (3:1). Rendement : 82%. PF:
181e183 ꢀC
1H: 7.68 (1H, d, J ¼ 15.3 Hz, CH]CH); 7.58 (1H, d, J ¼ 15.3 Hz, CH]CH); 2.73 (3H, s, CH3). 13C: 179.03 (C]O); 152.58 (C]N);
þ
139.84 (CH]CH); 121.85 (CH]CH); 18.13 (CH3). ESþ SM: 342 [MþH ]. Recristallisation : ethanol. Rendement : 84%. PF: 207
ꢀ
e209 ꢀC
1H: 7.68 (1H, d, J ¼ 15.3 Hz, CH]CH); 7.58 (1H, d, J ¼ 15.3 Hz, CH]CH); 2.73 (3H, s, CH3). 13C: 180.03 (C]O); 152.58 (C]N);
139.90 (CH]CH); 121.85 (CH]CH); 18.13 (CH3). ESþ SM: 281 [MþHþ]. Recristallisation : hexane/DCM (3:1). Rendement : 75%. PF:
192e194 ꢀC
5x
5y
3-NO2
4-NO2
1H: 7.80 (1H, d,J¼ 15.3 Hz, CH]CH); 7.70 (1H, d,J¼ 15.3 Hz, CH]CH); 2.85 (3H, s, CH3). 13C: 178.96 (C]O); 152.81 (C]N); 134.16
(CH]CH); 121.88 (CH]CH); 18.13 (CH3). ES þ SM: 308 [MþHþ]. Recristallisation : ethanol. Rendement : 65%. PF: 219e221 ꢀC
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1H: 7.68 (1H, d, J ¼ 15.3 Hz, CH]CH); 7.50 (2H, d, J ¼ 15.3 Hz, CH]CH); 2.83 (3H, s, CH3). 13C: 178.06 (C]O); 153.01 (C]N);
134.34 (CH]CH); 121.0 (CH]CH); 18.20 (CH3). ESþ SM: 308 [MþHþ]. Recristallisation : butanol. Rendement : 80%. PF: >260 ꢀ
C
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Please cite this article in press as: M. Ouattara, et al., Composes a structure imidazopyridinyl-arylpropenone, nouveaux agents