1168
AKYÜZ
3.5.2 | N-ethyl-2-[(4-oxoquinazolin-3(4H)-
yl)acetyl]hydrazinecarbothioamide (5b)
3.5.5 | N-(4-fluorophenyl)-
2-[(4-oxoquinazolin-3(4H)-yl)acetyl]
hydrazinecarbothioamide (5e)
Yield 70%, Mp: 226-228ꢀC, IR(vmax, cm−1): 3324-3300
(NH-NH), 1660-1612 (C O), 1590 (C N), 1182 (C S).
1H-NMR spectrum (400 MHz, DMSO-d6), δ, ppm (J, Hz):
10.30 (1H, s, NH), 9.70 (1H, s, NH), 8.09 (1H, t,
J = 7.6 Hz, Ar H), 7.90 (1H, s, NH), 7.81 (1H, t,
J = 7.6 Hz, Ar H), 7.49-7.63 (2H, m, Ar H), 7.21-7.33 (3H,
m, Ar H), 4.74 (2H, s, NCH2), 4.56 (2H, m, CH2), 4.15
(2H, s, CH2), 1.02 (3H, t, J = 8.0 Hz, CH3). 13C-NMR
(100 MHz, DMSO-d6), δ, ppm: 14.67 (CH3), 41.28 (CH2),
41.62 (CH2), 44.81 (NCH2), Ar C [120.11, 126.57, 126.64,
127.27, 127.32, 128.99, 129.20, 135.20, 135.20, 135.38,
135.69, 147.16], 156.42 (C N), 162.14 (C O), 167.26
(C O). LC-MS, m/z: 395.48 [M + H]+, 417.94
[M + Na]+.
Yield 65%, Mp: 238-240ꢀC (dec.) IR(vmax
,
cm−1):
3301-3035 (NH-NH), 1657 (C O), 1590 (C N), 1178
(C S). 1H-NMR spectrum: 10.51 (1H, s, NH), 9.78 (1H, s,
NH), 8.10 (1H, d, J = 8.0 Hz, Ar H), 7.90 (1H, s, NH),
7.82 (2H, t, J = 8.0 Hz, Ar H), 7.63-7.53 (1H, m, Ar H),
7.17–7.33 (4H, m, Ar H), 4.84 (2H, s, NCH2), 4.19 (2H, s,
CH2). 13C-NMR spectrum: 41.22 (CH2), 41.83 (NCH2), Ar
C [115.52, 120.13, 126.57, 127.38, 127.49, 129.14, 129.29,
135.24, 135.44, 135.78, 136.12, 147.39], 156.53 (C N),
159.90 (C-F, d, JCF = 250 Hz), 166.38 (C O), 167.56
(C O). LC–MS, m/z: 461.80 [M + H]+.
3.6 | Synthesis of compounds 6a-e
3.5.3 | N-phenyl-2-[(4-oxoquinazolin-3
(4H)-yl)acetyl]
hydrazinecarbothioamide (5c)
The compound derivates of thiosemicarbasite (0.01 mol)
were dissolved with cold H2SO4 in the ice bath. The mix-
ture was stirred in ice bath about an hour and then
nearly an hour at room temperature too. At the end of
this reaction, the mixture was taken in a beaker filled
with ice and the product was precipitated by neutralized
with NH3. White solid products were filtered off and rec-
rystallized from ethanol.
Yield 64%, Mp: 240ꢀC (dec.). IR(vmax
,
cm−1):
3310-3300 (NH-NH), 1656 (C O), 1589 (C N), 1179
(C S), 1H-NMR spectrum: 10.30 (1H, s, NH), 9.74
(1H, s, NH), 8.10 (2H, m, ArH), 7.85 (1H, s, NH), 7.80
(3H, m, Ar H), 7.65 (2H, t, J = 8.0 Hz, Ar H), 7.16-7.40
(5H, m, Ar H), 4.84 (2H, s, NCH2), 4.32 (2H, t,
J = 8.0 Hz, CH2). 13C-NMR spectrum: 40.78 (CH2),
44.83 (NCH2), Ar C [120.08, 126.57, 126.64, 127.33,
127.45, 128.99, 129.09, 129.24, 135.21, 135.38, 136.08,
139.38, 147.33], 156.43 (C N), 164.14 (C O), 166.51
(C O), 179.90 (C S). LC–MS, m/z: 443.94 [M + H]+,
465.99 [M + Na]+.
3.7 | 1. 2-benzyl-3-{[5-(methylamino)-
1,3,4-thiadiazol-2-yl]methyl}quinazolin-4
(3H)-one (6a)
Yield 55%, Mp: 154-156ꢀC. IR(vmax, cm−1): 3334 (NH),
1
1660 (C O), 1591-1568 (C N). H-NMR spectrum: 8.13
(1H, d, J = 8.0 Hz, Ar H); 7.80 (1H, s, Ar H); 7.72 (1H, s,
NH); 7.62 (2H, d, J = 8.0 Hz, Ar H); 7.51 (1H, s, Ar H);
7.30 (4H, m, Ar H); 7.16 (2H, t, J = 7.2 Hz, Ar H); 5.31
(2H, s, NCH2); 4.35 (2H, s, CH2); 2.81 (3H, s, CH3).
13C-NMR spectrum: 31.68 (CH3); 41.08 (CH2); 42.51
(CH2); Ar C [120.14, 126.70, 127.45, 128. 87, 129.03,
129.25, 135.18, 135.29, 135.87, 147.19]; 152.25 (thiadiazole
C2); 155.68 (C N); 161.65 (C O); 171.24 (thiadiazole C5).
LC-MS, m/z: 362.83 [M + H]+, 399.86 [M + Na]+.
3.5.4 | N-(4-nitrophenyl)-
2-[(4-oxoquinazolin-3(4H)-yl) acetyl]
hydrazinecarbothioamide (5d)
Yield 55%, Mp: 210ꢀC (dec.). IR(vmax, cm−1): 3462-3216
(NH-NH), 1671 (C O), 1594 (C N), 1176 (C S). 1H-
NMR spectrum: 10.70 (1H, s, NH), 10.0 (1H, s, NH), 8.12
(1H, d, J = 8.0 Hz, Ar H), 7.93 (1H, s, NH), 7.82 (2H, t,
J = 8.0 Hz, Ar H), 7.63–7.53 (1H, m, Ar H), 7.21–7.31
(4H, m, Ar H), 4.84 (2H, s, NCH2), 4.21 (2H, s, CH2). 13C-
NMR spectrum: 42.26 (CH2), 46.83 (NCH2), ArC [120.06,
126.57, 126.25, 127.28, 127.45, 129.17, 129.24, 135.21,
135.24, 135.95, 147.31], 156.29 (C N), 161.74 (C O),
164.62 (C O). LC–MS, m/z: 489.16 [M + H]+, 510.65
[M + Na]+.
3.7.1 | 2-benzyl-3-{[5-(ethylamino)-
1,3,4-thiadiazol-2-yl]methyl}quinazolin-4
(3H)-one (6b)
Yield 65%, Mp: 188-190ꢀC. IR(vmax, cm−1): 3180 (NH),
1
1669 (C O), 1590-1567 (C N). H-NMR spectrum: 8.13