S. Madapa, D. Sridhar, G. P. Yadav, P. R. Maulik, S. Batra
FULL PAPER
ppm. 13C NMR (CDCl3, 50 MHz): δ = 108.7, 115.9, 123.8, 125.9,
128.5, 128.9, 129.0, 129.3, 130.2, 130.4, 131.2, 132.0, 137.5, 138.4,
145.7, 156.9, 157.8, 168.1 ppm. ESI-MS: m/z = 357.3/359.2 [M +
1]+. HR-EIMS: calcd. for C22H13ClN2O 356.0716; found 356.0711.
3-(4-Bromophenyl)-4-(p-tolyl)isoxazolo[4,3-c]quinoline (6b): This
compound was isolated in 18% yield (0.08 g from 0.50 g) as a yel-
low solid, m.p. 218–220 °C. Rf (20% EtOAc/hexanes) = 0.74. 1H
NMR (CDCl3, 200 MHz): δ = 2.38 (s, 3 H, CH3), 7.07–7.21 (m, 4
H, ArH), 7.33–7.39 (m, 4 H, ArH), 7.62 (t, J = 7.3 Hz, 1 H, ArH),
7.77 (t, J = 7.2 Hz, 1 H, ArH), 8.10 (d, J = 8.0 Hz, 1 H, ArH),
8.50 (d, J = 7.3 Hz, 1 H, ArH) ppm. 13C NMR (CDCl3, 50 MHz):
δ = 21.8, 108.8, 115.9, 123.8, 125.9, 126.4, 128.3, 129.3, 129.5,
130.3, 131.4, 131.8, 131.9, 135.6, 140.4, 145.8, 156.2, 157.87,
168.1 ppm. ESI-MS: m/z = 415.2/417.1 [M + 1]+. C23H15BrN2O
(415.28): calcd. C 66.52, H 3.64, N 6.75; found C 66.54, H 3.50, N
6.90.
3-(4-Bromophenyl)-4-phenylisoxazolo[4,3-c]quinoline (5b): This
compound was isolated in 19% yield (0.072 g from 0.42 g) as a
yellow solid, m.p. 132–133 °C. Rf (20% EtOAc/hexanes) = 0.82. 1H
NMR (CDCl3, 300 MHz): δ = 7.50–7.51 (m, 2 H, ArH), 7.52–7.53
(m, 3 H, ArH), 7.55–7.56 (m, 3 H, ArH), 7.58–7.62 (m, 2 H, ArH),
8.02–8.05 (m, 3 H, ArH) ppm. 13C NMR (CDCl3, 50 MHz): δ =
121.3, 123.5, 127.2, 127.4, 128.5, 130.9, 131.7, 132.5, 136.8, 142.1,
188.9 ppm. ESI-MS: m/z = 401.2/403.1 [M + 1]+. C22H13BrN2O
(401.25): calcd. C 65.85, H 3.27, N 6.98; found C 65.54, H 3.09, N
7.16.
3-(4-Chlorophenyl)-4-phenyl-3,5-dihydroisoxazolo[4,3-c]quinoline
(7a): This compound was isolated in 57% yield (0.30 g from 0.60 g)
as a yellow solid, m.p. 220–222 °C. Rf (20 % EtOAc/hexanes) =
0.32. 1H NMR (CDCl3, 300 MHz): δ = 6.69 (s, 1 H, CH), 7.07 (dd,
3-(2,3-Dichlorophenyl)-4-phenylisoxazolo[4,3-c]quinoline (5c): This
compound was isolated in 19% yield (0.081 g from 0.48 g) as a
light brown solid, m.p. 200–201 °C. Rf (20% EtOAc/hexanes) =
2
1J = 1.9, J = 6.5 Hz, 2 H, ArH), 7.11–7.17 (m, 1 H, ArH), 7.19
1
2
(dd, J = 1.8, J = 6.7 Hz, 2 H, ArH), 7.34–7.39 (m, 4 H, ArH),
7.42–7.48 (m, 3 H, ArH), 7.70 (dd, 1J = 1.1, 2J = 7.8 Hz, 1 H,
ArH), 10.20 (s, 1 H, NH) ppm. 13C NMR (CDCl3, 75 MHz): δ =
80.7, 111.5, 115.6, 116.6, 122.0, 123.1, 1215.8, 126.3, 126.8, 127.3,
127.7, 127.9, 128.7, 130.2, 131.4, 132.1, 135.6, 138.7, 139.3,
1
0.82. H NMR (CDCl3, 300 MHz): δ = 7.08–7.18 (m, 4 H, ArH),
7.30–7.32 (m, 1 H, ArH), 7.39–7.41 (m, 2 H, ArH), 7.53–7.56 (m,
1 H, ArH), 7.69 (t, J = 7.5 Hz, 1 H, ArH), 7.84 (t, J = 7.4 Hz, 1
H, ArH), 8.17 (d, J = 8.1 Hz, 1 H, ArH), 8.56 (d, J = 7.8 Hz, 1 H,
ArH) ppm. 13C NMR (CDCl3, 50 MHz): δ = 111.2, 116.0, 123.9,
124.6, 127.5, 128.2, 128.6, 128.7, 129.8, 130.0, 130.4, 130.5, 132.1,
132.9, 134.3, 137.7, 145.8, 156.8, 157.2, 166.0 ppm. ESI-MS: m/z =
391.2/393.2 [M + 1]+. C22H12Cl2N2O (391.24): calcd. C 67.54, H
3.09, N 7.16; found C 67.66, H 3.41, N 7.39.
150.5 ppm. IR (KBr): ν
= 3300 (NH) cm–1. ESI-MS: m/z =
˜
max
359.2/361.2 [M + 1]+. C22H15ClN2O (358.82): calcd. C 73.64, H
4.21, N 7.81; found C 73.53, H 4.40, N 7.65.
3-(4-Bromophenyl)-4-phenyl-3,5-dihydroisoxazolo[4,3-c]quinoline
(7b): This compound was isolated in 17 % yield (0.063 g from
0.42 g) as a yellow solid, m.p. 227–229 °C. Rf (20% EtOAc/hexanes)
= 0.4. 1H NMR (CDCl3, 200 MHz): δ = 6.68 (s, 1 H, CH), 7.01
(d, J = 8.0 Hz, 2 H, ArH), 7.14 (t, J = 7.3 Hz, 1 H, ArH), 7.32–
7.37 (m, 5 H, ArH), 7.43–7.46 (m, 3 H, ArH), 7.70 (d, J = 7.7 Hz,
1 H, ArH), 10.19 (s, 1 H, NH) ppm. 13C NMR (CDCl3, 50 MHz):
δ = 80.7, 111.5, 115.6, 116.6, 120.1, 122.0, 123.1, 126.8, 127.7,
128.2, 128.7, 130.2, 132.1, 135.6, 138.7, 139.7, 150.5 ppm. IR
3-(2,4-Dichlorophenyl)-4-phenylisoxazolo[4,3-c]quinoline (5d): This
compound was isolated in 17% yield (0.075 g from 0.50 g) as a pale
yellow solid, m.p. 128–129 °C. Rf (20% EtOAc/hexanes) = 0.81. 1H
NMR (CDCl3, 300 MHz): δ = 7.09–7.21 (m, 4 H, ArH), 7.30–7.36
1
2
(m, 1 H, ArH), 7.38–7.43 (m, 3 H, ArH), 7.67 (dt, J = 1.1, J =
7.8 Hz, 1 H, ArH), 7.82 (dt, J = 1.5, 2J = 7.3 Hz, 1 H, ArH), 8.15
1
(d, J = 8.3 Hz, 1 H, ArH), 8.54 (dd, 1J = 1.3, 2J = 7.8 Hz, 1 H,
ArH) ppm. 13C NMR (CDCl3, 75 MHz): δ = 109.6, 114.3, 122.2,
125.7, 126.6, 126.9, 127.2, 127.4, 128.4, 128.5, 128.8, 130.4, 131.3,
133.7, 136.1, 136.4, 144.1, 155.1, 155.6, 163.9 ppm. ESI-MS: m/z =
391.2/393.1 [M + 1]+. C22H12Cl2N2O (391.24): calcd. C 67.54, H
3.09, N 7.16; found C 67.88, H 3.20, N 7.08.
(KBr): ν
= 3432 (NH) cm–1. ESI-MS: m/z = 403.2/405.1 [M +
˜
max
1]+. C22H15BrN2O (403.27): calcd. C 65.52, H 3.75, N 6.95; found
C 65.54, H 3.79, N 7.11.
3-(2,3-Dichlorophenyl)-4-phenyl-3,5-dihydroisoxazolo[4,3-c]quin-
oline (7c): This compound was isolated in 49% yield (0.21 g from
0.48 g) as a yellow solid, m.p. Ͼ250 °C. Rf (20% EtOAc/hexanes)
3-(3,4-Dichlorophenyl)-4-phenylisoxazolo[4,3-c]quinoline (5e): This
compound was isolated in 19% yield (0.085 g from 0.50 g) as a
yellow solid, m.p. 201–202 °C. Rf (20% EtOAc/hexanes) = 0.75. 1H
NMR (CDCl3, 300 MHz): δ = 7.15–7.18 (m, 1 H, ArH), 7.25–7.28
(m, 1 H, ArH), 7.33–7.38 (m, 3 H, ArH), 7.46–7.50 (m, 3 H, ArH),
7.68 (t, J = 7.5 Hz, 1 H, ArH), 7.82 (t, J = 7.5 Hz, 1 H, ArH), 8.15
(d, J = 8.1 Hz, 1 H, ArH), 8.53 (d, J = 7.8 Hz, 1 H, ArH) ppm.
13C NMR (CDCl3, 50 MHz): δ = 109.1, 115.8, 123.8, 127.0, 128.6,
128.8, 129.1, 129.2, 130.4, 130.6, 131.9, 132.2, 133.1, 135.7, 138.3,
145.6, 156.6, 157.8, 166.4 ppm. ESI-MS: m/z = 391.2/393.2 [M +
1]+. C22H12Cl2N2O·2H2O (427.28): calcd. C 64.56, H 3.45, N 6.84;
found C 64.80, H 3.41, N 6.79.
1
= 0.36. H NMR (CDCl3, 200 MHz): δ = 7.04 (s, 1 H, CH), 7.16–
7.19 (m, 3 H, ArH), 7.31–7.34 (m, 3 H, ArH), 7.40–7.47 (m, 5 H,
ArH), 7.69 (d, J = 7.8 Hz, 1 H, ArH), 10.36 (s, 1 H, NH) ppm.
13C NMR (CDCl3, 50.32 MHz): δ = 80.1, 112.5, 115.4, 117.9,
123.3, 124.3, 127.7, 128.6, 128.8, 129.9, 130.5, 131.5, 132.0, 133.3,
137.2, 139.9, 140.2, 152.1 ppm. IR (KBr): ν
= 3434 (NH) cm–1.
˜
max
ESI-MS: m/z = 393.1/395.1 [M + 1]+. C22H14Cl2N2O (393.26):
calcd. C 67.19, H 3.59, N 7.12; found C 67.34, H 3.66, N 7.01.
3-(2,4-Dichlorophenyl)-4-phenyl-3,5-dihydroisoxazolo[4,3-c]quin-
oline (7d): This compound was isolated in 52% yield (0.23 g from
0.50 g) as a yellow solid, m.p. 230–231 °C. Rf (20% EtOAc/hexanes)
3-(4-Chlorophenyl)-4-(p-tolyl)isoxazolo[4,3-c]quinoline (6a): This
compound was isolated in 14% yield (0.08 g from 0.65 g) as a yel-
low solid, m.p. 232–234 °C. Rf (20% EtOAc/hexanes) = 0.72. 1H
NMR (CDCl3, 200 MHz): δ = 7.09 (d, J = 7.8 Hz, 2 H, ArH), 7.22
(s, 4 H, ArH), 7.36 (d, J = 7.8 Hz, 2 H, ArH), 7.63 (t, J = 7.2 Hz,
1 H, ArH), 7.78 (t, J = 7.2 Hz, 1 H, ArH), 8.11 (d, J = 8.0 Hz, 1
H, ArH), 8.50 (d, J = 7.5 Hz, 1 H, ArH) ppm. 13C NMR (CDCl3,
50 MHz): δ = 21.8, 108.8, 115.9, 123.8, 126.0, 128.3, 129.3, 129.5,
130.3, 131.3, 131.9, 135.7, 137.5, 140.4, 145.8, 156.9, 157.8,
168.0 ppm. ESI-MS: m/z = 370.2/372.1 [M + 1]+. C23H15ClN2O
(370.83): calcd. C 74.49, H 4.08, N 7.55; found C 74.54, H 4.19, N
7.35.
1
= 0.28. H NMR (CDCl3, 200 MHz): δ = 6.96 (s, 1 H, CH), 7.10–
7.21 (m, 3 H, ArH), 7.30–7.33 (m, 3 H, ArH), 7.37–7.46 (m, 5 H,
ArH), 7.67 (d, J = 7.7 Hz, 1 H, ArH), 10.30 (s, 1 H, NH) ppm.
13C NMR (CDCl3, 75 MHz): δ = 82.6, 116.0, 119.0, 121.5, 126.9,
127.9, 131.3, 131.5, 132.4, 133.5, 135.0, 135.3, 136.9, 137.1, 137.2,
140.4, 140.7, 143.5, 155.7 ppm. IR (KBr): ν
= 3421 (NH) cm–1.
˜
max
ESI-MS: m/z = 393.1/395.0 [M + 1]+. C22H14Cl2N2O (393.26):
calcd. C 67.19, H 3.59, N 7.12; found C 66.98, H 3.42, N 7.23.
3-(3,4-Dichlorophenyl)-4-phenyl-3,5-dihydroisoxazolo[4,3-c]quin-
oline (7e): This compound was isolated in 47% yield (0.21 g from
0.50 g) as a yellow solid, m.p. 195–197 °C. Rf (20% EtOAc/hexanes)
4348
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Eur. J. Org. Chem. 2007, 4343–4351