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2H); 6.89 (d, J ¼ 9.0 Hz, 2H); 7.13 (t, J ¼ 8.9 Hz, 2H); 7.33 (dd,
J ¼ 8.4 Hz, J ¼ 5.8 Hz, 2H); 7.49 (d, J ¼ 9.0 Hz, 2H); 8.41 (t, J ¼ 5.6 Hz,
1H); 9.87 (s,1H); EIMS m/z 316 (Mþ). Anal. Calcd for C17H17FN2O3: C,
64.55; H, 5.42; F, 6.01; N, 8.86; found: C, 64.48; H, 5.43; F, 6.03; N,
8.88.
C17H18N2O4: C, 64.96; H, 5.77; N, 8.91; found: C, 64.91; H, 5.78; N,
8.92.
4.4.2.28. N2-[(4-Hydroxyphenyl)acetyl]-N-(4-nitrophenyl)glycina-
mide (3bb). White powder, 51%, mp 240e242 ꢁC, 1H NMR
(400 MHz, DMSO-d6): 3.39 (s, 2H); 3.95 (d, J ¼ 5.8 Hz, 2H); 6.69 (d,
J ¼ 8.4 Hz, 2H); 7.08 (d, J ¼ 8.4 Hz, 2H); 7.83 (d, J ¼ 9.3 Hz, 2H); 8.24
(d, J ¼ 9.2 Hz, 2H); 8.38 (t, J ¼ 5.7 Hz, 1H); 9.25 (s, 1H); 10.65 (s, 1H);
EIMS m/z 329 (Mþ). Anal. Calcd for C16H15N3O5: C, 58.36; H, 4.59; N,
12.76; found: C, 58.32; H, 4.59; N, 12.79.
4.4.2.22. N2-[(4-Fluorophenyl)acetyl]-N-(4-nitrophenyl)glycinamide
(3av). White powder, 70%, mp 246e248 ꢁC, 1H NMR (400 MHz,
DMSO-d6): 3.53 (s, 2H); 3.98 (d, J ¼ 5.7 Hz, 2H); 7.14 (t, J ¼ 8.9 Hz,
2H); 7.33 (dd, J ¼ 8.4 Hz, J ¼ 5.8 Hz, 2H); 7.84 (d, J ¼ 9.2 Hz, 2H); 8.25
(d, J ¼ 9.2 Hz, 2H); 8.52 (t, J ¼ 5.6 Hz, 1H); 10.67 (s, 1H); 13C NMR
(100 MHz, DMSO-d6): 40.42; 43.44; 115.37 (d, J ¼ 20.9 Hz); 119.18;
125.55; 131.38 (d, J ¼ 7.9 Hz); 132.81 (d, J ¼ 3.2 Hz); 142.63; 145.51;
161.50 (d, J ¼ 240.3 Hz); 169.29; 171.15; EIMS m/z 331 (Mþ). Anal.
Calcd for C16H14FN3O4: C, 58.01; H, 4.26; F, 5.73; N, 12.68; found: C,
58.06; H, 4.25; F, 5.72; N, 12.66.
4.4.2.29. N2-[(3-Hydroxyphenyl)acetyl]-N-(4-methoxyphenyl)glyci-
namide (3bc). White powder, 69%, mp 156e157 ꢁC, 1H NMR
(400 MHz, DMSO-d6): 3.42 (s, 2H); 3.72 (s, 3H); 3.87 (d, J ¼ 5.7 Hz,
2H); 6.62 (d, J ¼ 7.5 Hz,1H); 6.71 (d, J ¼ 6.4 Hz,1H); 6.72 (s,1H); 6.89
(d, J ¼ 8.9 Hz, 2H); 7.08 (t, J ¼ 8.0 Hz, 1H); 7.49 (d, J ¼ 8.9 Hz, 2H);
8.33 (t, J ¼ 5.4 Hz, 1H); 9.32 (s, 1H); 9.85 (s, 1H); 13C NMR (100 MHz,
DMSO-d6): 42.58; 43.10; 55.59; 113.79; 114.32; 116.52; 120.23;
121.07; 129.55; 132.47; 137.96; 155.63; 157.65; 167.64; 171.02; EIMS
m/z 314 (Mþ). Anal. Calcd for C17H18N2O4: C, 64.96; H, 5.77; N, 8.91;
found: C, 65.01; H, 5.76; N, 8.89.
4.4.2.23. N2-[(3-Fluorophenyl)acetyl]-N-(4-methoxyphenyl)glycina-
mide (3aw). White powder, 79%, mp 153e155 ꢁC, 1H NMR
(400 MHz, DMSO-d6): 3.56 (s, 2H); 3.72 (s, 3H); 3.89 (d, J ¼ 5.7 Hz,
2H); 6.89 (d, J ¼ 9.0 Hz, 2H); 7.07 (dt, J ¼ 8.6 Hz, J ¼ 2.1 Hz, 1H); 7.15
(t, J ¼ 8.2 Hz, 2H); 7.32e7.38 (m, 1H); 7.49 (d, J ¼ 9.0 Hz, 2H); 9.88 (s,
1H); 13C NMR (100 MHz, DMSO-d6): 42.03; 43.10; 55.59; 113.63 (d,
J ¼ 20.6 Hz); 114.33; 116.31 (d, J ¼ 21.3 Hz); 121.10; 125.75 (d,
J ¼ 2.7 Hz); 130.47 (d, J ¼ 8.3 Hz); 132.46; 139.53 (d, J ¼ 7.9 Hz);
155.64; 162.49 (d, J ¼ 241.4 Hz); 167.59; 170.53; EIMS m/z 316 (Mþ).
Anal. Calcd for C17H17FN2O3: C, 64.55; H, 5.42; F, 6.01; N, 8.86;
found: C, 64.49; H, 5.42; F, 6.03; N, 8.87.
4.4.2.30. N2-[(3-Hydroxyphenyl)acetyl]-N-(4-nitrophenyl)glycina-
mide (3bd). White powder, 60%, mp 197e198 ꢁC, 1H NMR
(400 MHz, DMSO-d6): 3.43 (s, 2H); 3.97 (d, J ¼ 5.7 Hz, 2H); 6.63 (d,
J ¼ 7.8 Hz, 1H); 6.71 (d, J ¼ 6.4 Hz, 1H); 6.72 (s, 1H); 7.09 (t,
J ¼ 8.0 Hz, 1H); 7.84 (d, J ¼ 9.2 Hz, 2H); 8.24 (d, J ¼ 9.1 Hz, 2H); 8.45
(t, J ¼ 5.6 Hz, 1H); 9.33 (s, 1H); 10.66 (s, 1H); 13C NMR (100 MHz,
DMSO-d6): 42.48; 43.45; 113.83; 116.53; 119.18; 120.22; 125.55;
129.57; 137.84; 142.63; 145.52; 157.66; 169.31; 171.22; EIMS m/z
329 (Mþ). Anal. Calcd for C16H15N3O5: C, 58.36; H, 4.59; N, 12.76;
found: C, 58.41; H, 4.58; N, 12.74.
4.4.2.24. N2-[(3-Fluorophenyl)acetyl]-N-(4-nitrophenyl)glycinamide
(3ax). White powder, 56%, mp 232e233 ꢁC, 1H NMR (400 MHz,
DMSO-d6): 3.57 (s, 2H); 3.99 (d, J ¼ 5.7 Hz, 2H); 7.07 (dt, J ¼ 8.7 Hz,
J ¼ 2.4 Hz, 1H); 7.13e7.16 (m, 2H); 7.32e7.38 (m, 1H); 7.84 (d,
J ¼ 9.2 Hz, 2H); 8.24 (d, J ¼ 9.2 Hz, 2H); 8.57 (t, J ¼ 5.6 Hz, 2H); 10.68
(s,1H); EIMS m/z 331 (Mþ). Anal. Calcd for C16H14FN3O4: C, 58.01; H,
4.26; F, 5.73; N, 12.68; found: C, 58.06; H, 4.26; F, 5.74; N, 12.70.
4.4.2.31. N2-[(2-Hydroxyphenyl)acetyl]-N-(4-methoxyphenyl)glyci-
namide (3be). White powder, 57%, mp 184e186 ꢁC, 1H NMR
(400 MHz, DMSO-d6): 3.48 (s, 2H); 3.72 (s, 3H); 3.88 (d, J ¼ 5.6 Hz,
2H); 6.75 (t, J ¼ 7.4 Hz, 1H); 6.81 (d, J ¼ 7.9 Hz, 1H); 6.89 (d,
J ¼ 9.0 Hz, 2H); 7.07 (td, J ¼ 7.8 Hz, J ¼ 1.5 Hz, 1H); 7.13 (dd,
J ¼ 7.4 Hz, J ¼ 1.2 Hz, 1H); 7.48 (d, J ¼ 9.0 Hz, 2H); 8.23 (t, J ¼ 5.6 Hz,
1H); 9.67 (s, 1H); 9.81 (s, 1H); EIMS m/z 329 (Mþ). Anal. Calcd for
4.4.2.25. N2-[(3,4-Dimethoxyphenyl)acetyl]-N-(4-methoxyphenyl)
glycinamide (3ay). White powder, 72%, mp 167e168 ꢁC, 1H NMR
(400 MHz, DMSO-d6): 3.44 (s, 2H); 3.72 (s, 3H); 3.73 (s, 3H); 3.75 (s,
3H); 3.87 (d, J ¼ 5.3 Hz, 2H); 6.80 (d, J ¼ 8.2 Hz, 1H); 6.86e6.90 (m,
3H); 6.95 (s, 1H); 7.49 (d, J ¼ 7.2 Hz, 2H); 8.32 (bs, 1H); 9.86 (s, 1H);
13C NMR (100 MHz, DMSO-d6): 42.15; 43.10; 55.59; 55.82; 55.97;
112.15; 113.39; 114.33; 121.03; 121.52; 129.12; 132.50; 147.90;
148.91; 155.62; 167.71; 171.34; EIMS m/z 358 (Mþ). Anal. Calcd for
C17H18N2O4: C, 64.96; H, 5.77; N, 8.91; found: C, 64.88; H, 5.78; N,
8.93.
4.4.2.32. N2-[(3-Chlorophenyl)acetyl]-N-(4-methylphenyl)glycina-
mide (3bf). White powder, 38%, mp 173e174 ꢁC, 1H NMR (500 MHz,
DMSO-d6): 2.25 (s, 3H); 3.55 (s, 2H); 3.90 (d, J ¼ 5.7 Hz, 2H); 7.11 (d,
J ¼ 8.3 Hz, 2H); 7.26 (d, J ¼ 7.4 Hz, 1H); 7.30 (d, J ¼ 8.1 Hz, 1H); 7.34
(t, J ¼ 7.6 Hz, 1H); 7.39 (s, 1H); 7.46 (d, J ¼ 8.3 Hz, 2H); 8.44 (t,
J ¼ 5.6 Hz, 1H); 9.90 (s, 1H); EIMS m/z 316 (Mþ). Anal. Calcd for
C
19H22N2O5: C, 63.67; H, 6.19; N, 7.82; found: C, 63.67; H, 6.19; N,
7.82.
4.4.2.26. N2-[(3,4-Dimethoxyphenyl)acetyl]-N-(4-nitrophenyl)glyci-
namide (3az). White powder, 75%, mp 224e226 ꢁC, 1H NMR
(400 MHz, DMSO-d6): 3.45 (s, 2H); 3.73 (s, 3H); 3.75 (s, 3H); 3.97 (d,
J ¼ 5.8 Hz, 2H); 6.81 (dd, J ¼ 8.2 Hz, J ¼ 1.8 Hz, 1H); 6.88 (d,
J ¼ 8.2 Hz, 1H); 6.94 (d, J ¼ 1.7 Hz, 1H); 7.83 (d, J ¼ 9.2 Hz, 2H); 8.24
(d, J ¼ 9.2 Hz, 2H); 8.42 (t, J ¼ 5.8 Hz, 1H); 10.66 (s, 1H); 13C NMR
(100 MHz, DMSO-d6): 42.03; 42.46; 55.84; 55.98; 112.16; 113.37;
119.16; 121.51; 125.56; 128.99; 142.63; 145.54; 147.91; 148.91;
169.39; 171.51; EIMS m/z 373 (Mþ). Anal. Calcd for C18H19N3O6: C,
57.90; H, 5.13; N, 11.25; found: C, 57.85; H, 5.14; N, 11.27.
C17H17ClN2O2: C, 64.46; H, 5.41; Cl,11.19; N, 8.84; found: C, 64.54; H,
5.41; Cl, 11.17; N, 8.83.
4.4.2.33. N2-[(4-Methylphenyl)acetyl]-N-(4-nitrophenyl)glycinamide
(3bg). Light yellow powder, 47%, mp over 300 ꢁC, 1H NMR
(500 MHz, DMSO-d6): 2.27 (s, 3H); 3.48 (s, 2H); 3.96 (d, J ¼ 5.8 Hz,
2H); 7.11 (d, J ¼ 7.9 Hz, 2H); 7.19 (d, J ¼ 7.9 Hz, 2H); 7.83 (d,
J ¼ 9.2 Hz, 2H); 7.19 (d, J ¼ 9.2 Hz, 2H); 8.42 (t, J ¼ 5.7 Hz, 1H); 10.63
(s, 1H); EIMS m/z 327 (Mþ). Anal. Calcd for C17H17N3O4: C, 62.38; H,
5.23; N, 12.84; found: C, 62.16; H, 5.24; N, 12.87.
4.4.2.27. N2-[(4-Hydroxyphenyl)acetyl]-N-(4-methoxyphenyl)glyci-
namide (3ba). White powder, 53%, mp 216e220 ꢁC, 1H NMR
(400 MHz, DMSO-d6): 3.37 (s, 2H); 3.72 (s, 3H); 3.85 (d, J ¼ 5.8 Hz,
2H); 6.68 (d, J ¼ 8.4 Hz, 2H); 6.89 (d, J ¼ 9.0 Hz, 2H); 7.08 (d,
J ¼ 8.4 Hz, 2H); 7.48 (d, J ¼ 9.0 Hz, 2H); 8.27 (t, J ¼ 5.6 Hz, 1H); 9.34
(bs, 1H); 9.86 (s, 1H); EIMS m/z 314 (Mþ). Anal. Calcd for
Acknowledgments
The work was financed by grants from National Natural Science
Foundation of China (grant No. 21262013), by a Project supported
by Hunan Provincial Natural Science Foundation of China (grant No.