434
RADHIKA et al.
mp 114–121°C. IR spectrum, ν, cm–1: 2928, 1602,
1519, 1346. 1H NMR (400 MHz, DMSO-d6) δ 2.5 (s,
3H, CH3), 2.9 (dd, 1H, CH2), 4.0 (dd, 1H, CH2), 5.0
(td, 1H, CH), 6.9–7.4 (m, 3H, Ar–H), 7.6 (S, 1H,
NH), 7.8–8.2 (m, 4H, Ar–H). 13C NMR (100 MHz,
DMSO-d6) δ 172.8, 161.6, 152.7, 148.8, 142.5, 136.2,
127.5, 126.4, 114.5, 109.1, 52.8, 43.4, 13.3. ESI-MS:
m/z 339 (M + 1) observed for C17H14N4O4. Anal.
calcd.: C, 60.35; H, 4.17; N, 16.56; O, 18.92. Found:
C, 61.04; H, 4.07, N, 15.79; O, 19.10.
line), 5.6 (td, 1H, pyrazoline), 6.8–7.1 (m, 4H, ArH),
7.2–7.5 (m, 5H, Ar–H), 7.8–8.2 (m, 4H, ArH).
13C NMR (100 MHz, DMSO-d6) δ 170.0, 165.3,
160.4, 158.2, 148.5, 136.1, 134.2, 132.3, 128.9, 128.2,
127.5, 127.0, 126.7, 125.7, 114.7, 109.7, 62.8, 56.7,
42.3, 13.1. ESI-MS: m/z 483 (M + 1) observed for
C27H22N4O5. Anal. calcd.: C, 67.21; H, 4.60; N, 11.61;
O, 16.58. Found: C, 65.26; H, 5.78; N, 11.51; O, 17.68.
(5-(4-Chlorophenyl)-3-(5-methyl-3-(4-nitrophe-
nyl)isoxazol-4-yl)-1H-pyrazol-1-yl)(phenyl)metha-
none (VII): Yield 71%, mp 100–110°C. IR spectrum,
4-(5-(2,4-Dichlorophenyl)-4,5-dihydro-1H-pyra-
zol-3-yl)-5-methyl-3-(4-nitrophenyl)isoxazole (Vg).
Yield 69%, mp 126–131°C. IR spectrum, ν, cm–1:
1
ν, cm–1: 2922, 1629, 1520, 1348, 750. H NMR
(400 MHz, DMSO-d6) δ 2.6 (s, 3H, CH3), 2.9 (dd,
1H, CH2), 3.9 (dd, 1H, CH2), 5.7 (td, 1H, CH), 6.8–
7.0 (m, 4H, ArH), 7.1–7.4 (m, 5H, ArH), 7.6–8.1 (m,
4H, ArH). 13C NMR (100 MHz, DMSO-d6) δ 169.4,
166.1160.4, 158.6, 148.3, 139.3, 137.2, 135.6, 132.5,
132.1, 128.9, 128.0, 127.5, 126.5, 125.9, 109.5, 66.9,
42.7, 13. ESI-MS: m/z 488 (M + 1) observed for
C26H19ClN4O4. Anal. calcd.: C, 64.14; H, 3.93; Cl,
7.28; N, 11.51, O, 13.14. Found: C, 65.14; H, 4.20; Cl,
6.98; N, 10.56; O, 13.02.
1
2930, 1600, 1520, 1348, 752. H NMR (400 MHz,
DMSO-d6) δ 2.6 (s, 3H, CH3), 3.0 (dd, 1H, CH2), 3.9
(dd, 1H, CH2), 5.1 (td, 1H, CH), 7.0–7.4 (m, 4H,
ArH), 7.6 (s, H, NH), 7.8–8.2 (m, 3H, ArH).
13C NMR (100 MHz, DMSO-d6) δ 172.1, 165.6,
152.04, 151.1, 148.9, 142.5, 136.3, 127.1, 126.5, 124.5,
120.2, 109.8, 51.4, 41.9, 13.2. ESI-MS: m/z 418 (M + 1)
observed for C19H15Cl2N4O3. Anal. calcd.: C, 54.69;
H, 3.38; Cl, 16.99; N, 13.43; O, 11.50. Found: C,
54.24; H, 3.69; Cl, 17.20; N, 13.72; O, 11.15.
4-(5-(2, 4-Methoxy phenyl)-4, 5-dihydro-1H-pyr-
azol-3-yl)-5-methyl-3-(4-nitrophenyl)isoxazole (Vh).
Yield 71%, mp 121–125°C. IR spectrum, ν, cm–1:
2929, 1600, 1520, 1348, 1240, 1030. 1H NMR
(400 MHz, DMSO-d6) δ 2.7 (s, 3H, CH3), 3.7 (s, 3H,
OCH3), 3.8 (s, 3H, OCH3), 3.0 (dd, 1H, CH2), 3.9
(dd, 1H, CH2), 5.0 (td, 1H, CH), 6.8–7.4 (m, 4H,
ArH), 7.6 (s, H, NH), 7.8–8.4, 8.2–8.4 (m, 3H, ArH).
13C NMR (100 MHz, DMSO-d6) δ 170.6, 161.4,
158.6, 157.1, 155.7, 148.3, 135.9, 133.6, 128.9, 127.2,
125.4, 121.6, 115.5, 109.6, 62.3, 51.4, 43.6, 13.4. ESI-
MS: m/z 409 (M + 1) observed for C21H20N4O5. Anal.
calcd.: C, 61.76; H, 4.94; N, 13.72; O, 19.59. Found:
C, 60.92; H, 5.04; N, 13.76; O, 20.28.
(3-(5-Methyl-3-(4-nitrophenyl)isoxazol-4-yl)-5-p-
tolyl-1H-pyrazol-1-yl)(phenyl)methanone (VIII). Yield
72%, mp 125–137°C. IR spectrum, ν, cm–1: 2923,
1
1629, 1520, 1348. H NMR (400 MHz, DMSO-d6) δ
2.4 (s, 3H, CH3), 2.6 (s, 3H, CH3), 2.9 (dd, 1H, CH2),
3.8 (dd, 1H,CH2), 5.7 (td, 1H, CH), 7.1–7.3 (m, 6H,
Ar–H), 7.4 (t, 2H, Ar–H), 7.6–8.1 (m, 5H, Ar–
H).13C NMR (100 MHz, DMSO-d6) δ 170.0, 169.4,
158.1, 152.8, 148.2, 139.1, 136.6, 135.7, 133.7, 130.7,
128.5, 127.6, 127.0, 126.4, 123.3, 109.5, 62.4, 42.4,
21.5, 13.1. ESI-MS: m/z 467 (M + 1) observed for
C27H22N4O4. Anal. calcd.: C, 69.52, H, 4.75, N, 12.01,
O, 13.72. Found: C, 68.01; H, 5.12, N, 11.45; O, 15.42.
(5-(4-Fluorophenyl)-3-(5-methyl-3-(4-nitrophe-
nyl)isoxazol-4-yl)-1H-pyrazol-1-yl)(phenyl)metha-
none (IX). Yield 70%, mp 98–100°C. IR spectrum,
5-Methyl-3-(4-nitrophenyl)-4-(5-(pyridine-3-yl)-
4,5-dihydro-1H-pyrazol-3-yl)isoxazole (Vi). Yield
71%, mp 118–122°C. IR spectrum, ν, cm–1: 2930,
1
ν, cm–1: 2993, 1629, 1520, 1348, 1000. H NMR
(400 MHz, DMSO-d6) δ 2.7 (s, 3H, CH3), 3.1 (dd,
1H, CH2), 4.1 (dd, 1H, CH2), 5.8 (td, 1H, CH), 6.8–
7.2 (m, 4H, Ar–H), 7.4–7.6 (m, 4H, ArH), 7.8–8.1
(m, 5H, Ar–H).13C NMR (100 MHz, DMSO-d6) δ
169.4, 165.3, 162.5, 158.8, 148.5, 139.7, 137.7, 134.2,
132.3, 128.9, 127.5, 127.0, 126.7, 125.9, 114.7, 109.2,
62.8, 42.3, 13.1. ESI-MS: m/z 471 (M + 1) observed
for C26H19FN4O4. Anal. calcd.: C, 66.38; H, 4.07; F,
4.04; N, 11.91; O, 13.60. Found: C, 67.05; H, 5.12; F,
3.98; N, 12.01; O, 11.84.
1
1602, 1524, 1348. H NMR (400 MHz, DMSO-d6) δ
2.5 (s, 3H, CH3), 2.9 (dd, 1H, CH2), 4.0 (dd, 1H,
CH2), 5.0 (td, 1H, CH), 7.2–7.4 (m, 2H, ArH), 7.6 (s,
H, NH), 7.8–8.4 (m, 6H, ArH). 13C NMR (100 MHz,
DMSO-d6) δ 171.5, 160.9, 152.1, 150.1, 148.5, 145.2,
135.1, 132.4, 127.5, 124.9, 122.2, 109.8, 59.4, 42.9,
13.5. ESI-MS: m/z 350 (M + 1) observed for
C18H15N5O3. Anal. calcd.: C, 61.89; H, 4.33; N, 20.05;
O, 13.74. Found: C, 61.56; H, 4.12; N, 21.02; O, 13.3.
(5-(1-Thiophen2-yl)-3-(5-methyl-3-(4-nitrophe-
nyl)isoxazol-4-yl)-1H-pyrazol-1-yl)(phenyl)metha-
none (X): Yield 74%, mp 99–112°C. IR spectrum, ν,
(5-(4-Methoxyphenyl)-3-(5-methyl-3-(4-nitrophe-
nyl)isoxazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)(phe-
nyl)methanone (VI): Yield 77%, mp 120–135°C. IR
spectrum, ν, cm–1: 2929, 1629, 1520, 1348, 1240,
1
cm–1: 2993, 1629, 1520, 1348. H NMR (400 MHz,
DMSO-d6) δ 2.7 (s, 3H, CH3), 2.9 (dd, 1H, CH2), 4.0,
(dd, 1H, CH2), 5.8 (td, 1H, CH), 6.8–7.3 (m, 3H,
Ar–H), 7.6–7.9 (m, 5H, ArH), 7.9–8.3 (m, 4H,
1
1030. H NMR (400 MHz, DMSO-d6) δ 2.6 (s, 3H,
CH3), 3.7 (s, 3H, OCH3), 3.8, 3.0 (dd, 2H, pyrazo-
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY
Vol. 46
No. 3
2020