HARUTYUNYAN et al.
1368
160°C, Rf 0.62. IR spectrum, ν, cm–1: 1672 (C=O),
1631 (C=C–C=N). 1H NMR spectrum, δ, ppm (J, Hz):
1.30 d (6H, CH3, J = 6.9), 2.95 sept (1H, CH, J = 6.9),
2.99–3.06 m (2H, CH2C6H5), 4.43–4.50 m (2H,
NCH2), 7.02 d (1H, =CH, J = 15.2), 7.15–7.29 m (7H,
Harom), 7.39 d.d (1H, =CH, J = 8.6, 0.3), 7.50–7.54 m
(2H, C6H4), 7.83 d (1H, =CH, J = 15.2), 7.97 d.d (1H,
=CH, J = 8.6, 2.1), 8.45 d.d (1H, =CH, J = 2.1, 0.6).
Found, %: C 62.23; H 4.64; N 5.22. C27H25IN2O. Cal-
culated, %: C 62.31; H 4.84; N 5.38.
2.0), 7.45 d.d.d (1H, Harom, J = 8.0, 6.7, 1.6), 7.71–
7.80 m (2H, Harom), 8.12 d (1H, =CH, J = 15.5),
8.15 d.d (1H, Harom, J = 8.0, 1.2). 13C NMR spectrum,
δC, ppm: 39.8 (2C, NMe2), 111.9, 120.7, 123.4, 124.4,
125.8, 126.3, 127.0, 127.1, 127.9, 128.6, 129.0, 132.0,
132.8, 133.5, 134.2, 134.4, 147.0, 149.8, 151.0, 161.0.
Found %: C 65.98; H 4.28; N 9.58. C24H19Cl2N3O.
Calculated, %: C 66.06; H 4.39; N 9.63.
2-[(E)-2-(4-Chlorophenyl)ethenyl]-3-(3-methyl-
1-phenyl-1H-pyrazol-5-yl)quinazolin-4(3H)-one (5c)
was synthesized by reaction of quinazoline 3c with
4-chlorobenzaldehyde. Yield 50.5%, mp 216–218°C,
Rf 0.51. IR spectrum, ν, cm–1: 1682 (C=O), 1636
6-Iodo-2-[(E)-2-(1-methyl-1H-indol-3-yl)-
ethenyl]-3-(2-phenylethyl)quinazolin-4(3H)-one (4g)
was synthesized by reaction of quinazoline 2 with
1-methyl-1H-indole-3-carbaldehyde. Yield 50.2%,
mp 198–200°C, Rf 0.48. IR spectrum, ν, cm–1: 1665
1
(C=C–C=N). H NMR spectrum, δ, ppm (J, Hz): 2.46
s (3H, CH3), 6.35 d (1H, =CH, J = 15.4), 6.39 br.s (1H,
4′-H), 7.22–7.30 m (5H, C6H5), 7.34–7.43 m (4H,
C6H4Cl), 7.48 d.d.d (1H, Harom, J = 7.9, 7.2, 1.1),
7.66 br.d (1H, Harom, J = 8.1), 7.80 d.d.d (1H, Harom, J =
8.1, 7.2, 1.5), 7.81 d (1H. =CH, J = 15.4), 8.14 d.d
(1H, Harom, J = 7.9, 1.5). 13C NMR spectrum, δC, ppm:
13.7, 106.3, 118.1, 119.5, 122.7, 126.4, 126.6, 127.1,
127.3, 128.6, 128.6, 128.7, 133.1, 133.4, 134.5, 134.7,
137.5, 139.0, 146.8, 148.5, 150.0, 160.3. Found, %:
C 71.04; H 4.28; N 12.68. C26H19ClN4O. Calculated,
%: C 71.15; H 4.36; N 12.77.
1
(C=O), 1621 (C=C–C=N). H NMR spectrum, δ, ppm
(J, Hz): 3.06–3.11 m (2H, CH2), 3.91 s (3H, CH3),
4.45–4.50 m (2H, NCH2), 7.01 d (1H, =CH, J = 15.0),
7.17–7.44 m (9H, Harom), 7.75 s (1H, =CHN), 7.85–
7.88 m (1H, Harom), 7.93 d.d (1H, Harom, J = 8.6, 2.2),
8.20 d (1H, =CH, J = 15.0), 8.43 d (1H, Harom, J = 2.2).
Found, %: C 60.96; H 4.08; N 7.82. C27H22IN3O. Cal-
culated, %: C 61.03; H 4.17; N 7.91.
2-[(E)-2-(4-Chlorophenyl)ethenyl]-3-[4-(di-
methylamino)phenyl]quinazolin-4(3H)-one (5a) was
synthesized by reaction of quinazoline 3a with
4-chlorobenzaldehyde. Yield 52.4%, mp 210–212°C,
Rf 0.51. IR spectrum, ν, cm–1: 1678 (C=O), 1633
2-[(E)-2-(2,4-Dichlorophenyl)ethenyl]-
3-(3-methyl-1-phenyl-1H-pyrazol-5-yl)quinazolin-
4(3H)-one (5d) was synthesized by reaction of
quinazoline 3c with 2,4-dichlorobenzaldehyde. Yield
49.7%, mp 206–208°C, Rf 0.43. IR spectrum, ν, cm–1:
1694 (C=O), 1631 (C=C–C=N). 1H NMR spectrum, δ,
ppm (J, Hz): 2.44 s (3H, CH3), 6.40 s (1H, 4′-H),
6.43 d (1H, =CH, J = 15.4), 7.22–7.34 m (6H, Harom),
7.44–7.53 m (3H, Harom), 7.70 br.d (1H, Harom, J = 8.1),
7.81 br.d.d.d (1H, Harom, J = 8.1, 7.1, 1.4), 8.06 d
(1H, =CH, J = 15.4), 8.15 br.d (1H, Harom, J = 7.9).
13C NMR spectrum, δC, ppm: 13.7, 106.3, 119.6,
121.0, 122.8, 126.7, 127.3, 127.4, 128.5, 129.1, 131.4,
133.2, 134.3, 134.4, 134.6, 134.9, 137.5, 146.6, 148.5,
149.6, 160.2. Found, %: C 65.91; H 3.78; N 11.78.
C26H18Cl2N4O. Calculated, %: C 65.97; H 3.83;
N 11.84.
1
(C=C–C=N). H NMR spectrum, δ, ppm (J, Hz):
3.09 s (6H, NCH3), 6.44 d (1H, =CH, J = 15.5), 6.80–
6.85 m (2H, C6H4NMe2), 7.05–7.10 m (2H,
C6H4NMe2), 7.29–7.36 m (4H, C6H4Cl), 7.43 d.d.d
(1H, Harom, J = 7.9, 7.0, 1.3), 7.68 br.d (1H, Harom, J =
8.2), 7.76 d.d.d (1H, Harom, J = 8.2, 7.0, 1.5), 7.87 d
(1H, =CH, J = 15.5), 8.14 d.d (1H, Harom, J = 7.9, 1.5).
13C NMR spectrum, δC, ppm: 39.8 (2C, NMe2), 111.9,
120.5, 120.6, 124.5, 125.5, 126.3, 126.7, 128.4 (2C,
CH), 128.4 (2C, CH), 128.6 (2C, CH), 133.5, 133.6,
134.2, 137.1, 147.2, 149.8, 151.4, 161.0. Found, %:
C 71.68; H 4.98; N 10.38. C24H20ClN3O. Calculated,
%: C 71.73; H 5.02; N 10.46.
2-[(E)-2-(2,4-Dichlorophenyl)ethenyl]-3-[(4-di-
methylamino)phenyl]quinazolin-4(3H)-one (5b) was
synthesized by reaction of quinazoline 3a with 2,4-di-
chlorobenzaldehyde. Yield 51.8%, mp 242–244°C,
Rf 0.53. IR spectrum, ν, cm–1: 1682 (C=O), 1630
4-{2-[(E)-2-(3-Nitrophenyl)ethenyl]-4-oxo-3,4-di-
hydroquinazolin-3-yl}benzenesulfonamide (5e) was
synthesized by reaction of quinazoline 3b with 3-nitro-
benzaldehyde. Yield 45.5%, mp 310–312°C, Rf 0.45.
IR spectrum, ν, cm–1: 3310 (NH2), 1655 (C=O), 1604
1
(C=C–C=N). H NMR spectrum, δ, ppm (J, Hz):
1
3.08 s (6H, NCH3), 6.49 d (1H, =CH, J = 15.5), 6.79–
6.84 m (2H, C6H4NMe2), 7.06–7.11 m (2H,
C6H4NMe2), 7.24 d.d (1H, C6H3Cl2, J = 8.5, 2.0),
7.29 d (1H, C6H3Cl2, J = 8.5), 7.44 d (1H, C6H3Cl2, J =
(C=C–C=N). H NMR spectrum, δ, ppm (J, Hz):
6.52 d (1H, CH=CH, J = 15.5), 7.33 br.s (2H, NH2),
7.50 d.d.d (1H, C6H4, J = 8.1, 7.1, 1.2), 7.52–7.57 m
(2H, C6H4SO2), 7.61 t (1H, 5′-H, J = 7.9), 7.72–7.78 m
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 9 2019