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Med Chem Res (2013) 22:340–350
2-(2-(4-Methylbenzylidene)hydrazinyl)-N-(4-(2-methyl-4-
oxoquinazolin-3(4H)-yl)phenyl)acetamide (5c)
and hydrazine hydrate (0.05 g, 0.01 mol) in 30 mL ethanol
was refluxed for 10 h on a water bath. Cool the resulting
solution, filtered, dried, and recrystallised from ethanol.
Yield: 77 % m.p. 215–217 ꢁC. IR: (KBr cm-1) 3428 (NH),
3075 (Ar–CH), 2952 (CH3–CH), 1723 (C=O quinazoline),
IR: (KBr cm-1) 3462 (NH), 3055 (Ar–CH), 2988 (CH3–
CH), 1751 (C=O quinazoline), 1666 (C=O amide), 1547
(CH=N). 1H-NMR (CDCl3, 300 MHz) d ppm: 9.90 (1H, s,
CONH), 8.46 (1H, s, CH=N), 6.84–8.01 (12H, m, Ar–CH),
4.49 (2H, s, CH2), 3.81 (1H, s, CH2NH), 2.92 (3H, s, CH3
benzylidene), 2.38 (3H, s, CH3). ESI–MS: MS: m/z 425.
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1650 (C=O amide). H-NMR (CDCl3, 300 MHz) d ppm:
9.85 (1H, s, CONH), 7.07–8.19 (8H, m, Ar–CH), 5.62 (2H,
s, NH2), 4.51 (1H, s, CH2NH), 4.06 (2H, d, CH2), 2.39 (3H,
s, CH3). ESI–MS: MS: m/z 323. Anal. Cald for
C17H17N5O2: C, 63.15; H, 5.30; N, 21.66. Found: C, 62.99;
H, 5.32; N, 21.73.
2-(2-(4-Chlorobenzylidene)hydrazinyl)-N-(4-(2-methyl-4-
oxoquinazolin-3(4H)-yl)phenyl)acetamide (5d)
General procedure for the synthesis of 5a–5j
IR: (KBr cm-1) 3443 (NH), 3028 (Ar–CH), 2946 (CH3–
CH), 1734 (C=O quinazoline), 1642 (C=O amide), 1530
(CH=N), 775 (C–Cl). 1H-NMR (CDCl3, 300 MHz) d ppm:
9.71 (1H, s, CONH), 8.65 (1H, s, CH=N), 7.12–8.08 (12H,
m, Ar–CH), 4.62 (2H, s, CH2), 3.94 (1H, s, CH2NH), 2.47
(3H, s, CH3). ESI–MS: MS: m/z 447 (M ? 2).
Title compound 5a–5j was synthesized by adding appro-
priate aromatic/heterocyclic aldehydes (0.01 mol) in
fraction with the well stirred mixture of 2-hydrazinyl-N-
(4-(2-methyl-4-oxoquinazolin-3(4H)-yl)phenyl)acetamide 4
(3.23 g, 0.01 mol) in 50 mL ethanol and 2–3 drops of
glacial acetic acid. The pH was maintained to 5–6. The
reaction mixture was then refluxed for a period of 4–6 h
and kept aside for about 2 h. The products were separated
by filtration, washed, and vacuum dried. Finally the prod-
ucts were recrystallized using ethanol to get pure form. The
method used for the preparation and isolation of the com-
pounds gave materials of good purity, as evidenced by their
spectral analyses and by TLC. The title compounds are
found to be soluble in chloroform, dimethyl sulfoxide, and
dimethylformamide. The physicochemical properties of the
synthesized compounds are given in Table 1.
2-(2-(4-(Trifluoromethyl)benzylidene)hydrazinyl)-N-(4-(2-
methyl-4-oxoquinazolin-3(4H)-yl)phenyl)acetamide (5e)
IR: (KBr cm-1) 3435 (NH), 3046 (Ar–CH), 2961 (CH3–
CH), 1738 (C=O quinazoline), 1650 (C=O amide), 1515
(CH=N), 1137 (C–F). 1H-NMR (CDCl3, 300 MHz) d ppm:
9.85 (1H, s, CONH), 8.33 (1H, s, CH=N), 7.04–8.19 (12H,
m, Ar–CH), 4.38 (2H, s, CH2), 3.72 (1H, s, CH2NH), 2.56
(3H, s, CH3). ESI–MS: MS: m/z 479.
2-(2-(4-Methoxybenzylidene)hydrazinyl)-N-(4-(2-methyl-4-
oxoquinazolin-3(4H)-yl)phenyl)acetamide (5f)
2-(2-Benzylidenehydrazinyl)-N-(4-(2-methyl-4-
oxoquinazolin-3(4H)-yl)phenyl)acetamide (5a)
IR: (KBr cm-1) 3468 (NH), 3032 (Ar–CH), 2950 (CH3–
CH), 1755 (C=O quinazoline), 1679 (C=O amide), 1524
IR: (KBr cm-1) 3454 (NH), 3037 (Ar–CH), 2973 (CH3–
CH), 1720 (C=O quinazoline), 1645 (C=O amide), 1531
(CH=N). 1H-NMR (CDCl3, 300 MHz) d ppm: 9.94 (1H, s,
CONH), 8.51 (1H, s, CH=N), 7.03–8.17 (13H, m, Ar–CH),
4.26 (2H, s, CH2), 3.74 (1H, s, CH2NH), 2.50 (3H, s, CH3).
ESI–MS: MS: m/z 411.
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(CH=N), 1061 (C–O–C). H-NMR (CDCl3, 300 MHz) d
ppm: 9.93 (1H, s, CONH), 8.77 (1H, s, CH=N), 6.90–7.92
(12H, m, Ar–CH), 4.70 (2H, s, CH2), 3.75 (1H, s, CH2NH),
3.44 (3H, s, OCH3), 2.31 (3H, s, CH3). ESI–MS: MS:
m/z 441.
2-(2-(4-Nitrobenzylidene)hydrazinyl)-N-(4-(2-methyl-4-
oxoquinazolin-3(4H)-yl)phenyl)acetamide (5g)
2-(2-(4-Fluorobenzylidene)hydrazinyl)-N-(4-(2-methyl-4-
oxoquinazolin-3(4H)-yl)phenyl)acetamide (5b)
IR: (KBr cm-1) 3450 (NH), 3074 (Ar–CH), 2989 (CH3–
CH), 1722 (C=O quinazoline), 1647 (C=O amide), 1542
(CH=N), 1505 and 1311 (C–NO2). 1H-NMR (CDCl3,
300 MHz) d ppm: 9.89 (1H, s, CONH), 8.62 (1H, s,
CH=N), 7.09–8.20 (12H, m, Ar–CH), 4.55 (2H, s, CH2),
3.98 (1H, s, CH2NH), 2.57 (3H, s, CH3). ESI–MS: MS:
m/z 456.
IR: (KBr cm-1) 3439 (NH), 3063 (Ar–CH), 2955 (CH3–
CH), 1747 (C=O quinazoline), 1674 (C=O amide), 1516
(CH=N), 1122 (C–F). 1H-NMR (CDCl3, 300 MHz) d ppm:
9.87 (1H, s, CONH), 8.70 (1H, s, CH=N), 7.21–8.26 (12H,
m, Ar–CH), 4.53 (2H, s, CH2), 3.92 (1H, s, CH2NH), 2.35
(3H, s, CH3). ESI–MS: MS: m/z 429.
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