exchangeable), 4.35 (d, 1H, J = 16.1Hz, α-CH), 5.80 (s, 1H,
sp3 C-H), 5.98 (s, 2H, CH2), 6.64 (t, 2H, J = 5.3 Hz, Ar-H),
6.67-6.85 (m, 1H, Ar-H), 6.87-6.93 (m, 2H, Ar-H),7.19 (s, 1H,
NH, D2O exchangeable), 7.22-7.25 (m, 1H, Ar-H), 7.59 (d, 1H,
J =7.6 Hz, Ar-H), 8.96 (s, 1H, NH, D2O exchangeable). 13C-
NMR (125 MHz: DMSO- d6): δ 40.18, 71.96, 101.80, 107.51,
108.58, 114.74, 117.69, 121.19, 128.10, 133.99, 134.18,
147.49, 148.08, 148.23, 163.44, 167.82. Anal. Calcd. for
C17H16N4O4: C, 59.99; H, 4.74; N, 16.46. Found: C, 59.73; H,
4.57; N, 16.29.
J = 5.3 Hz, Ar-H), 7.24 (s, 1H, NH, D2O exchangeable), 7.52-
7.57 (m, 2H, Ar-H), 9.63 (s, 1H, NH, D2O exchangeable).
Anal. Calcd. for C15H16N4O: C, 59.99; H, 5.37; N, 18.66.
Found: C, 60.25; H, 5.52; N, 18.91.
2-(2-(furan-2-yl)-1,2-dihydro-4-oxoquinazolin-3(4H)-yl)-3-
phenylpropanehydrazide 20
Compound 20 was obtained as grey powder. Method A:
0.32 g (85%); yield; Method B: 0.35 g (93%); yield; mp 145-
146 ºC.IR (KBr): 3465, 3313 (NH + NH2), 1660 (C=O, amide),
1
1623 (C=O, amide) cm-1. H-NMR (500 MHz: DMSO-d6): δ
2-(2-(furan-2-yl)-4-oxo-1,2-dihydroquinazolin-3(4H)-
2.98 (d, 2H, J = 7.6 Hz, CH2), 4.25 (brs, 2H, NH2, D2O
exchangeable), 4.57 (q, 1H, J=7.6Hz, α- CH), 5.92 (brs, 1H,
sp3 C-H), 6.22 (s, 2H, Ar-H), 6.45 (t, 1H, J = 7.6 Hz, Ar-H),
6.63 (d, 1H, J = 7.6 Hz, Ar-H), 7.07 (t, 1H, J = 7.6 Hz, Ar-H),
7.13 (t, 1H, J = 6.9 Hz, Ar-H) ,7.23-7.30 (m, 5H, 4Ar-H +
(NH, D2O exchangeable), 7.45 (d, 1H, J =7.6Hz, Ar-H), 8.18
(d, 1H, J =8.4Hz, Ar-H), 9.24 (s, 1H, NH, D2O exchangeable).
Anal. Calcd. for C21H20N4O3: C, 67.01; H, 5.36; N, 14.88.
Found: C, 67.28; H, 5.51; N, 14.63.
yl)acetohydrazide 16
Compound 16 was obtained as pale brown crystals. Method
A: 0.22 g (76.8%) yield, Method B: 0.26 g (92.9%) yield, mp
65-66ºC. IR (KBr): 3728, 3284 (NH+NH2), 1678 (C=O,
amide), 1637 (C=O, amide) cm-1. 1H-NMR (500 MHz: DMSO-
d6): δ 4.14 (s, 2H, NH2, D2O exchangeable), 4.61 (d, 1H, J =
16.8 Hz, α-CH), 4.89 (d, 1H, J = 16.8 Hz, α-CH), 5.91 (brs,
1H, sp3 C-H), 6.35-6.69 (m, 1H, Ar-H), 6.66-6.69 (m, 2H, Ar-
H), 7.23-7.38 (m, 2H, Ar-H + (1NH, D2O exchangeable)),
7.49-7.68 (m, 3H, Ar-H), 11.04 (s, 1H, NH, D2O
exchangeable). Anal. Calcd. for C14H14N4O3: C, 58.73; H,
4.93; N, 19.57. Found: C, 58.99; H, 4.70; N, 19.32.
2-(2-(4-Chlorophenyl)-1,2-dihydro-4-oxoquinazolin-3(4H)-yl)-
3-phenylpropanehydrazide 21
Compound 21 was obtained as white crystals. Method A:
0.31 g (73%) yield. Method B: 0.39 g (91.8%) yield; mp 85-
86ºC; IR (KBr): 3476 (NH), 3372, 3307 (NH2), 1723 (C=O,
amide), 1633 (C=O, amide) cm-1. 1H-NMR (500 MHz: DMSO-
d6): δ 3.07-3.09 (m, 2H, CH2), 3.59 (s, 2H, NH2, D2O
exchangeable), 4.55-4.57 (m, 1H, CH), 6.28 (s, 1H, sp3C-H),
6.46 (t, 1H, J = 7.6 Hz, Ar-H), 6.62 (d, 1H, J = 7.6 Hz, Ar-H),
7.09 (t, 2H, J = 6.8 Hz, Ar-H), 7.15-7.17 (m, 1H, NH, D2O
exchangeable), 7.20-7.25 (m, 5H, Ar-H), 7.43 (d, 1H, J = 6.1
Hz, Ar-H), 7.56 (d, 2H, J = 6.8 Hz, Ar-H), 7.87 (d, 1H, J = 8.4
Hz, Ar-H), 8.65 (s, 1H, NH, D2O exchangeable). Anal. Calcd.
for C23H21ClN4O2: C, 65.63; H, 5.03; N, 13.31. Found: C,
65.89; H, 4.87; N, 13.17.
2-(2-(4-chlorophenyl)-1,2-dihydro-4-oxoquinazolin-3(4H)-
yl)acetohydrazide 17
Compound 17 was obtained as colorless crystals. Method
A: 0.29 g (87.7%) yield; Method B: 0.31 g (93.7%) yield; mp
158-159 ºC. IR (KBr): 3338, 3229 (NH2), 3042 (NH), 1700
(C=O, amide), 1657 (C=O, amide) cm-1. H-NMR (500 MHz:
1
DMSO-d6): δ 3.61 (d, 1H, J = 17.5 Hz, α-CH), 4.02 (s, 2H,
NH2, D2O exchangeable), 4.33 (d, 1H, J = 17.5 Hz, α-CH),
5.96 (s, 1H, sp3.C-H), 6.65-6.67 (m, 2H, Ar-H), 7.23-7.37 (m,
1H, Ar-H), 7.41-7.43 (m, 5H, 4 Ar-H + (1NH, D2O
exchangeable)), 7.56-7.62 (m, 1H, Ar-H), 9.63 (s, 1H, NH,
D2O exchangeable). Anal. Calcd. for C16H15ClN4O2: C, 58.10;
H, 4.57; N, 16.94. Found: C, 58.34; H, 4.82; N, 17.18.
3-(1,2-Dihydro-4-oxo-2-phenylquinazolin-3(4H)-
yl)propanehydrazide 31
2-(2-(4-methoxyphenyl)-4-oxo-1,2-dihydroquinazolin-3(4H)-
Compound 31 was obtained as colorless crystals. Method
A: 0.26 g (83.8%) yield; Method B: 0.30 g (96.7%) yield; mp
126-127 ºC; IR (KBr): 3445, 3302 (NH + NH2), 1733 (C=O,
amide), 1631 (C=O, amide) cm-1. 1H-NMR (500 MHz: DMSO-
d6): δ 2.44-2.46 (m, 1H, CH), 2.62-2.66 (m, 1H, CH), 3.03-
3.08 (m, 1H, CH), 3.53 (s, 2H, NH2, D2O exchangeable), 3.90-
3.93 (m, 1H, CH), 5.88 (s, 1H, sp3 C-H), 6.56-6.63 (m, 2H, Ar-
H), 7.16 (t, 1H, J = 6.9 Hz, Ar-H), 7.28-7.35 (m, 6H, 5Ar-H +
1NH, D2O exchangeable), 7.59 (d, 1H, J = 8.4 Hz, Ar-H), 8.97
(s, 1H, NH, D2O exchangeable). Anal .Calcd. for C17H18N4O2:
C, 65.79; H, 5.85; N, 18.05. Found: C, 65.53; H, 5.69; N,
18.28.
yl)acetohydrazide 18
Compound 18 was obtained as yellow crystals. Method A:
0.26 g (79.7%) yield; Method B: 0.30 g (92%) yield; mp 187-
188ºC; IR (KBr): 3437, 3296 (NH+NH2), 1672 (C=O, amide),
1
1633 (C=O, amide) cm-1. H-NMR (500 MHz: DMSO-d6): δ
3.07 (d, 1H, J = 16.1 Hz, α-CH), 3.70 (s, 3H, OCH3), 4.13 (s,
2H, NH2, D2O exchangeable), 4.35 (d, 1H, J = 16.1 Hz, α-CH),
5.83 (s, 1H, sp3 C-H), 6.64 (t, 2H, J = 8.4 Hz, Ar-H), 6.92 (d,
2H, J = 9.1 Hz, Ar-H), 7.12 (s, 1H, NH, D2O exchangeable),
7.20 (t, 1H, J = 6.9 Hz, Ar-H), 7.28 (d, 2H, J = 8.4 Hz, Ar-H),
7.59 (d, 1H, J = 8.4 Hz, Ar-H), 8.59 (s, 1H, NH, D2O
exchangeable). Anal. Calcd. for C17H18N4O3: C, 62.57; H,
5.56; N, 17.17. Found: C, 62.33; H, 5.31; N, 17.43.
3-(2-(Benzo[d][1,3]dioxol-5-yl)-1,2-dihydro-4-oxoquinazolin-
3(4H)-yl)propanehydrazide 32
2-(2-(furan-2-yl)-1,2-dihydro-4-oxoquinazolin-3(4H)-
Compound 32 was obtained as colorless crystals. Method
A: 0.28 g (79%) yield; Method B: 0.33 g (93%) yield; mp
155-156ºC; IR (KBr): 3728, 3304 (NH + NH2), 1732 (C=O,
amide), 1631 (C=O, amide) cm-1. 1H-NMR (500 MHz: DMSO-
d6): δ 2.46-2.49 (m, 1H, CH), 2.61-2.66 (m, 1H, CH), 3.03-
3.06 (m, 1H, CH), 3.54 (s, 2H, NH2, D2O exchangeable), 3.88-
3.91 (m, 1H, CH), 5.81 (brs, 1H, sp3 C-H), 5.96 (brs, 2H,
CH2), 6.57-6.63 (m, 2H, Ar-H), 6.72 (d, 1H, J = 7.6 Hz, Ar-H),
6.82-6.85 (m, 2H, Ar-H), 7.15-7.17 (m, 1H, Ar-H), 7.25 (s,
yl)propanehydrazide 19
Compound 19 was obtained as white crystals. Method A:
0.23 g (76.6%) yield; Method B: 0.28 g (93%) yield; mp 173-
174ºC; IR (KBr): 3423, 3344 (NH2), 3223 (NH), 1737 (C=O,
amide), 1634 (C=O, amide) cm-1; 1H-NMR (500 MHz: DMSO-
d6): δ 1.20 (d, 3H, J = 6.8 Hz, CH3), 4.14 (s, 2H, NH2, D2O
exchangeable), 4.33-4.35 (m, 1H, CH), 5.95 (s, 1H, sp3 C-H),
6.27-6.33 (m, 2H, Ar-H), 6.65-6.68 (m, 2H, Ar-H), 7.21 (t, 1H,