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Abid et al.
CH2); MS (GC, 70 eV): m/z (%): 358 (M + 1+,1),
357 (M+, 5), 223(10), 197(15), 196(83), 195(13), 179
(13), 167(12), 165(27), 152(16), 135(13), 134(27), 105
(100), 77(52), 51(11); HRMS (EI) calcd. for
C22H19N3O2 [M+]: 357.14718, Found: 357.1483.
C28H27N3O2 : C, 76.86; H, 6.22; N, 9.60, Found: C,
76.69; H, 6.17; N, 9.81; 1H NMR (DMSO-d6,
300 MHz); δ 12.11 (s, 1H, NH), 9.69 (s, 1H, NH), 8.79
(s, 1H, CH), 8.75 (d, 2H, J = 6.6 Hz, Ar–H), 8.18 (d,
2H, J = 6.3 Hz, Ar–H), 8.05 (d, 2H, J = 6.3 Hz, Ar–
H), 7.70–7.58 (m, 8H, Ar–H), 4.44 (dd, 1H,
J = 8.0,7.5 Hz, CH), 1.88–1.79 (m, 3H, CH/CH2), 0.92
(d, 3H, J = 6.3 Hz, CH3), 0.85 (d, 3H, J = 6.3 Hz,
CH3); MS (GC, 70 eV): m/z (%): 204(19), 203(100), 202
(12), 176(13), 174(8), 88(10), 75(8), 61(6); HRMS Pos
(ESI) calcd. for C28H27N3O2, [M + H]+ calcd.
438.13354, found 438.13364 and [M + Na]+ calcd.
460.11548, found 460.11583; exact ion mass 437.12626.
2-Benzamido-N0-(quinolin-2-ylmethylene)acetohydrazide 6c
Light brown powder; Yield: 93%; m.p:
226–229ꢀC; IR (cm−1): 3391 (NH), 1697 (C O),1641
(C N), 1538 (C C); Elemental analysis: calcd. for
C19H16N4O2: C, 68.66; H, 4.85; N, 16.86. Found: C,
68.83; H, 4.77; N, 16.72; 1H NMR (DMSO-d6,
300 MHz);
δ 11.90 (s, 1H, NH), 8.78 (t, 1H,
J = 6.6 Hz, NH), 8.42 (d, 1H, J = 8.7 Hz, Ar–H), 8.21
(s, 1H, CH), 8.14 (d, 1H, J = 8.7 Hz, Ar–H), 8.05–8.0
(m, 2H, Ar), 7.93 (d, 2H, J = 6.6 Hz, Ar–H), 7.80 (dt,
1H, J = 6.6, 2.7 Hz, Ar–H), 7.64 (dt, 1H, J = 6.6,
2.7 Hz, Ar–H), 7.57–7.50 (m, 3H, Ar–H), 4.53 (d, 2H,
J = 6.0 Hz, CH2); MS (GC, 70 eV): m/z (%): 290(5),
198(54), 170(62), 142(68), 115(82), 105(100), 77(71),
51(18); HRMS Pos (ESI) calcd. for C19H16N4O2
[M + H]+ calcd. 333.1346, Found: 333.13527 and
[M + Na]+ calcd. 355.11655, Found 355.11638; exact
ion mass 332.12733.
N0-(2,4-Dihydroxybenzylidene)-2-benzamido-4-methylpe-
ntanehydrazide 6h
Dark brown powder; Yield: 72%; m.p:
204–209ꢀC; IR (cm−1): 3318 (NH), 1688 (C O), 1651
(C N), 1561 (C C); Elemental analysis: calcd. for
C20H23N3O4: C, 65.03; H, 6.28; N, 11.37, Found: C,
65.16; H, 6.45; N, 11.20; 1H NMR (DMSO-d6,
300 MHz); δ 11.60 (s, 1H, NH), 9.33 (bs, 2H, OH),
8.54 (d, 1H, J = 8.7 Hz, NH), 8.27 (s, 1H, CH), 7.90
(d, 2H, J = 6.6 Hz, Ar–H), 7.57 (d, 1H, J = 6.6 Hz,
Ar–H), 7.53 (d, 2H, J = 6.3 Hz, Ar–H), 7.26 (d, 1H,
J = 3.0 Hz, Ar–H), 6.94 (dd, 1H, J = 6.3,3.0 Hz, Ar–
H), 6.79 (d, 1H, J = 8.7 Hz, Ar–H), 4.51 (dd, 1H,
J = 8.0, 7.5 Hz, CH), 1.94–1.88 (m, 3H, CH/CH2),
0.91 (d, 3H, J = 6.3 Hz, CH3), 0.87 (d, 3H, J = 6.3 Hz,
CH3); MS (GC, 70 eV): m/z (%): 256(22), 135(24), 122
(32), 105(100), 77(47), 51(14), 29(11); HRMS Pos (ESI)
calcd. for C20H23N3O4 [M + H]+ calcd. 370.17613,
Found 370.17713; [M + Na]+ calcd. 392.15808, Found
392.15769, exact ion mass 369.16886.
N0-(3,5-Dimethoxybenzylidene)-2-benzamidoacetohydraz-
ide 6d
Floral white powder; Yield: 91%; m.p: 174–175ꢀC;
IR (cm−1): 3255 (NH), 1687 (C O),1631 (C N), 1573
(C C); Elemental analysis: calcd. for C18H19N3O4: C,
63.33; H, 5.61; N, 12.31, Found: C, 63.47; H, 5.53; N,
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12.44; H NMR (DMSO-d6, 300 MHz); δ 11.51 (s, 1H,
NH), 8.70 (t, 1H, J = 6.6 Hz, NH), 7.93 (s, 1H, CH),
7.90 (d, 2H, J = 6.6 Hz, Ar–H), 7.56–7.49 (m, 3H, Ar),
6.86 (t, 2H, J = 3.0 Hz, Ar–H), 6.55(t, 1H, J = 3.0 Hz,
Ar–H), 4.42 (d, 2H, J = 6.3 Hz, CH2), 3.78 (s, 6H,
2OCH3); MS (GC, 70 eV): m/z (%): 341 (M+, 1), 207
(26),180(18), 178(11), 153(17), 135(11), 134(24),
105 (100), 77 (67), 51 (14); HRMS Pos (ESI) calcd. for
C18H19N3O4 [M + H]+; calcd. 342.14483, Found
342.14496, and [M + Na]+ calcd. 364.12678, Found
364.12699; exact ion mass 341.13756.
N0-(p-Biphenyl)-2-benzamido-4-methylpentanehydrazide 6i
Floral white powder, Yield: 89%; m.p: 234–238ꢀC;
IR (cm−1): 3345 (NH), 1672 (C O), 1619 (C N), 1558
(C C); Elemental analysis: calcd. for C26H27N3O2: C,
75.52; H, 6.58; N, 10.16, Found: C, 75.82; H, 6.73; N,
1
10.03; H NMR (DMSO-d6, 300 MHz);δ 11.89 (s, 1H,
NH), 8.52 (s, 1H, CH), 7.94 (d, 2H, J = 6.60 Hz, Ar–
H), 7.82–7.77 (m, 4H, Ar–H), 7.74 (d, 2H, J = 6.3 Hz,
Ar–H), 7.61–7.47(m, 5H, Ar–H), 7.42 (d, 1H,
J = 8.7 Hz, Ar–H), 4.55 (dd, 1H, J = 8.0,7.5 Hz, CH),
1.79–1.73 (m, 3H, CH/CH2), 0.92 (d, 3H, J = 6.3 Hz,
CH3), 0.85 (d, 3H, J = 6.3 Hz, CH3); MS (GC, 70 eV):
N0-(anthracene-10-ylmethylene)-2-benzamido-4-methylpe-
ntanehydrazide 6g
Dark orange powder; Yield: 79%; m.p:
225–230ꢀC; IR (cm−1): 3298 (NH), 1663 (C O), 1624
(C N), 1549 (C C); Elemental analysis: calcd. for
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© 2017 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J. Chin. Chem. Soc. 2017