ACCEPTED MANUSCRIPT
4.2.1. Acetic acid, 2-[ [3-(4-morpholinyl) propyl]amino]-2-oxo-,2-[(2-methoxylphenyl) methylene]
hydrazide (6a)
1
White solid, yield 63%. mp: 171-172 , purity:99.58%. H NMR (500 MHz, DMSO-d6) δ 12.15 (s,
1H), 9.10 (t, J = 5.4 Hz, 1H), 8.92 (s, 1H), 7.84 (d, J = 7.0 Hz, 1H), 7.44 (t, J = 7.3 Hz, 1H), 7.10 (d, J
= 8.3 Hz, 1H), 7.01 (t, J = 7.5 Hz, 1H), 3.85 (s, 3H), 3.62 – 3.57 (m, 4H), 3.25 (q, J = 6.4 Hz, 2H), 2.33
(dd, J = 12.8, 5.7 Hz, 6H), 1.69 – 1.62 (m, 2H).13C NMR (125 MHz, DMSO) δ 160.01, 158.52, 157.00,
146.83, 132.47, 126.26, 122.59, 121.16, 112.39, 66.62, 56.78, 56.23, 53.79, 38.39, 25.61. HRMS (ESI):
m/z calcd for C17H24N4O4 [M+H], 349.1870; found, 349.1887.
4.2.2. Acetic acid, 2-[[3-(4-morpholinyl)propyl]amino]-2-oxo-,2-[(3,4,5-trimethoxyphenyl)
methylene]hydrazide (6b)
1
White solid, yield 60%. mp: 206 , purity:99.25%. H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H),
9.13 (t, J = 5.7 Hz, 1H), 8.47 (s, 1H), 6.98 (s, 2H), 3.83 (s, 6H), 3.71 (s, 3H), 3.62 – 3.58 (m, 4H), 3.26
(q, J = 6.5 Hz, 2H), 2.39 – 2.32 (m, 6H), 1.66 (p, J = 6.7, 6.0 Hz, 2H).13C NMR (125 MHz, DMSO) δ
159.98, 156.88, 153.65, 151.18, 129.83, 105.02, 66.58, 60.60, 56.78, 56.45, 53.75, 38.45, 25.52.HRMS
(ESI): m/z calcd for C19H28N4O6 [M+H], 409.2082; found, 409.2099.
4.2.3. Acetic acid, 2-[ [3-(4-morpholinyl) propyl]amino]-2-oxo-,2-[(3-nitro-4-hydroxyphenyl)
methylene]hydrazide (6c)
1
Red solid, yield 58%. mp: 230-232 . purity:94.38%. H NMR (500 MHz, DMSO-d6) δ 12.23 (s,
1H), 9.24 (t, J = 5.8 Hz, 1H), 8.60 (s, 1H), 8.22 (s, 1H), 7.94 (d, J = 8.8 Hz, 1H), 7.23 (d, J = 8.7 Hz,
1H), 3.73 – 3.70 (m, 5H), 3.35 (q, J = 6.4 Hz, 2H), 2.52 (dd, J = 15.9, 8.9 Hz, 6H), 1.78 (p, J = 6.7 Hz,
2H). 13C NMR (125 MHz, DMSO-d6) δ 160.01, 156.84, 149.43, 137.52, 133.38, 125.10, 121.03, 66.35,
56.53, 53.57, 40.35, 38.24, 25.40. HRMS (ESI): m/z calcd for C16H21N5O6 [M+H], 380.1565; found,
380.1584.
4.2.4. Acetic acid, 2-[ [3-(4-morpholinyl) propyl]amino]-2-oxo-,2-[(2-hydroxyphenyl) methylene]
hydrazide (6d)
1
White solid, yield 69%. purity:96.34%. mp: 180-182 . H NMR (500 MHz, DMSO-d6) δ 12.53 (s,
1H), 11.14 (s, 1H), 9.25 (t, J = 5.6 Hz, 1H), 8.87 (s, 1H), 7.61 (d, J = 7.6 Hz, 1H), 7.42 (t, J = 7.7 Hz,
1H), 7.02 (t, J = 8.5 Hz, 2H), 3.73 – 3.66 (m, 4H), 3.36 (q, J = 6.3 Hz, 2H), 2.44 (dd, J = 13.3, 6.1 Hz,
6H), 1.76 (p, J = 6.6 Hz, 2H).13C NMR (125 MHz, DMSO-d6) δ 159.66 , 158.08 , 156.88 , 151.52 ,
132.32 , 130.07 , 119.86 , 118.98 , 116.93 , 66.59 , 56.73 , 53.75 , 38.40 , 25.58 . HRMS (ESI): m/z
calcd for C16H22N4O4 [M+H], 335.1714; found, 335.1712.
4.2.5. Acetic acid, 2-[ [3-(4-morpholinyl) propyl]amino]-2-oxo-,2-[(3,4-dimethoxyphenyl) methylene]
hydrazide (6e)
1
White solid, yield 70%. mp: 210-211 . purity:94.33%. H NMR (500 MHz, DMSO-d6) δ 12.10 (s,
1H), 9.25 – 9.19 (m, 1H), 8.59 (s, 1H), 7.40 (s, 1H), 7.27 (d, J = 8.1 Hz, 1H), 7.13 (d, J = 8.3 Hz, 1H),
3.91 (d, J = 2.7 Hz, 6H), 3.70 (s, 4H), 3.36 (q, J = 6.2 Hz, 2H), 2.50 – 2.40 (m, 6H), 1.76 (p, J = 6.2 Hz,
2H).13C NMR (125 MHz, DMSO) δ 160.07, 156.71, 151.60, 151.39, 149.56, 127.06, 122.79, 111.97,
108.93, 66.61, 56.81, 56.06, 55.98, 53.78, 38.46, 25.56. HRMS (ESI): m/z calcd for C18H26N4O5
[M+H], 379.1976; found, 379.1976.
12