ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
5
0
0
0
0
0
6
5
-Amino-3 -methyl-2-oxo-1 H-spiro[5-chloroindoline-3,4 -pyrano-[2,3-c]pyrazole]-
-carbonitrile (5b)
ꢁ
1 1
IR (KBr): 3396, 3136, 2182, 1714, 1644 cm ; H NMR (300 MHz, DMSO-d ): d 1.58
6
(
s, 3H, CH ), 6.92–6.93 (m, 1H, Ar), 7.23–7.24 (m, 1H, Ar), 7.29–7.31 (m, 3H, Ar,
3
NH ), 10.76 (s, 1H, NH), 12.35 (s, 1H, NH).
2
0
0
0
0
0
6
-Amino-3 -methyl-2-oxo-1 H-spiro[5-niroindoline-3,4 -pyrano[2,3-c]pyrazole]-5 -
carbonitrile (5c)
ꢁ
1 1
IR (KBr): 3450, 3322, 2193, 1731, 1644 cm ; H NMR (300 MHz, DMSO-d ): d 1.58
6
(
s, 3H, CH ), 7.13–7.15 (m, 1H, Ar), 7.43 (s, 2H, NH ), 7.91–7.92 (m, 1H, Ar),
3
2
8.23–8.25 (m, 1H, Ar), 11.37 (s, 1H, NH), 12.41 (s, 1H, NH).
0
0
0
0
0
6
-Amino-1,3 -dimethyl-2-oxo-1 H-spiro[indoline-3,4 -pyrano[2,3-c]pyrazole]-5 -
carbonitrile (5d)
ꢁ
1 1
IR (KBr): 3196, 3136, 2682, 1714, 1644 cm ; H NMR (300 MHz, DMSO-d ): d 1.45
6
(
(
s, 3H, CH ), 3.20 (3H, s, CH ), 7.06–7.14 (4H, m, Ar), 7.25 (2H, s, NH ), 7.31–7.41
3 3 2
1H, m, Ar), 12.29 (s, 1H, NH).
0
0
0
0
0
6
5
-Amino-3 -methyl-2-oxo-1 H-spiro[5-bromoindoline-3,4 -pyrano-[2,3-c]pyrazole]-
-carbonitrile (5e)
ꢁ
1 1
IR (KBr): 3391, 3138, 2181, 1713, 1642 cm ; H NMR (300 MHz, DMSO-d ): d 1.58
6
(
3H, s, CH ), 6.87–6.89 (m, 1H, Ar), 7.23–7.24 (m, 1H, Ar), 7.32 (s, 2H, NH ),
3
2
7.42–7.44 (m, 1H, Ar), 10.78 (s, 1H, NH), 12.35 (s, 1H, NH).
0
0
0
0
0
6
5
-Amino-1-benzyl-3 -methyl-2-oxo-1 H-spiro[indoline-3,4 -pyrano[2,3-c]pyrazole]-
-carbonitrile (5f)
ꢁ
1 1
IR (KBr): 31876, 3140, 2182, 1714, 1644 cm ; H NMR (300 MHz, DMSO-d ): d 1.35
6
(
7
s, 3H, CH ), 4.91 (d, 1H, J ¼ 15.6 Hz, CH Ph), 5.00 (d, 1H, J ¼ 15.6 Hz, CH Ph),
3
2
2
.00–7.14 (m, 3H, Ar), 7.23–7.36 (m, 6H, Ar, NH ), 7.37–7.44 (m, 2H, Ar), 12.30
2
(s, 1H, NH).
0
0
0
0
0
0
6
5
-Amino-3 -methyl-2-oxo-1 -phenyl-1 H-spiro[indoline-3,4 -pyrano[2,3-c]pyrazole]-
-carbonitrile (5g)
ꢁ1 1
IR (KBr): 3412, 3280, 3174, 2200, 1692, 1650, 1526, 1132 cm ; H NMR (300 MHz,
DMSO-d ): d 1.55 (s, 3H, CH ), 6.94 (d, J ¼ 7.4 Hz, 1H), 7.03 (t, J ¼ 7.6 Hz, 1H), 7.18
6
3
(
2
d, J ¼ 7.2 Hz, 1H), 7.28 (t, J ¼ 7.5 Hz,1H), 7.36 (t, J ¼ 7.6 Hz,1H), 7.52 (t, J ¼ 7.8 Hz,
H), 7.58 (br s, 2H, NH ), 7.79 (d, J ¼ 7.9 Hz, 2H), 10.76 (s,1H, NH).
2