6
-Amino-3-methyl-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (7a): gray solid;
mp 244-245 C. FT-IR (KBr): 3374, 3311, 3173, 2876, 2193, 1650, 1612, 1597, 1490, 1161, 1045, 746
cm . H NMR (500 MHz, DMSO-d ): δ = 12.00 (s, 1H, NH), 7.27-7.13 (m, 5H, ArH), 6.85 (s, 2H,
̊
-1 1
6
1
3
NH ), 4.53 (s, 1H, CH), 1.76 (s, 3H, CH ). C NMR (125 MHz, DMSO-d ): δ = 161.2, 155.2, 144.8,
2
3
6
1
35.9, 128.7, 127.8, 127.0, 121.1, 109.4, 87.7, 36.8, 10.1.
6
-Amino-4-(4-fluorophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
C. FT-IR (KBr): 3468, 3233, 3120, 2971, 2195, 1648, 1587, 1491, 1070,
010, 825 cm . H NMR (500 MHz, DMSO-d ): δ = 12.11 (s, 1H, NH), 7.11-7.19 (m, 4H, ArH), 6.89
(7b):
yellow solid; mp 241-243
̊
-1 1
1
6
1
3
(
s, 2H, NH ), 4.62 (s, 1H, CH), 1.77 (s, 3H, CH ). C NMR (125 MHz, DMSO-d ): δ = 162.3, 160.4
2 3 6
(d, J = 241.2 Hz), 161.2, 155.1, 141.12, 141.1, 136.0, 129.8, 129.7, 121.1, 105.2, 77.6, 35.9, 10.1.
6
-Amino-4-(4-bromophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
white solid; mp 179-180 C. FT-IR (KBr): 3478, 3235, 3119, 2971, 2193, 1648, 1597, 1492, 1396,
069, 1010, 825 cm . H NMR (500 MHz, DMSO-d ): δ = 12.12 (s, 1H, NH), 7.49 (d, 2H, J = 8.5
(7c):
̊
-1 1
1
6
1
3
Hz), 7.11 (d, 2H, J = 8.5 Hz), 6.92 (s, 2H, NH ), 4.61 (s, 1H, CH), 1.78 (s, 3H, CH ). C NMR (125
2
3
MHz, DMSO-d ): δ = 161.3, 155.1, 144.3, 136.1, 132.4, 131.8, 130.6, 130.1, 101.1, 84.1, 36.1, 10.2.
6
6
-Amino-4-(4-hydroxyphenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (7d):
yellow solid; mp 224-226 C. FT-IR (KBr): 3390, 3307, 3140, 2876, 2176, 1648, 1611, 1599, 1513,
̊
-
1 1
1
1
492, 1408, 1195, 1048, 812 cm . H NMR (500 MHz, DMSO-d ): δ = 12.03 (s, 1H, NH), 9.27 (s,
6
H, OH), 6.92 (d, 2H, J = 7.0 Hz), 6.78 (s, 2H, NH ), 6.66 (d, 2H, J = 7.0 Hz), 4.45 (s, 1H, CH), 1.76
2
1
3
(
s, 3H, CH ), C NMR (125 MHz, DMSO-d ): δ = 161.0, 156.4, 155.2, 139.4, 135.9, 135.2, 128.8,
3
6
1
15.5, 98.5, 88.2, 35.9, 10.2.
6
-Amino-4-(4-methoxyphenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (7e):
yellow solid; mp 210-211
̊
-
1
1
1
8
3
1
392, 1172, 1031, 804 cm . H NMR (500 MHz, DMSO-d ): δ = 12.05 (s, 1H, NH), 7.06 (d, 2H, J =
6
.5 Hz), 6.85 (d, 2H, J = 8.5 Hz), 6.79 (s, 2H, NH ), 4.52 (s, 1H, CH), 3.71 (s, 3H, OCH ), 1.77 (s,
2
3
H, CH3). 13C NMR (125 MHz, DMSO-d ): δ = 161.1, 158.4, 155.2, 136.9, 135.9, 128.9, 121.2,
6
14.2, 98.1, 79.8, 59.5, 35.9, 10.2.
6
-Amino-3-methyl-4-(4-nitrophenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
(7f):
brown solid; mp 220-222
̊
-
1 1
1
6
347, 1107, 1051, 852 cm . H NMR (500 MHz, DMSO-d ): δ = 12.17 (s, 1H, NH), 8.19 (d, 2H, J =
6
1
3
.0 Hz), 7.45 (d, 2H, J = 6.0 Hz), 7.01 (s, 2H, NH ), 4.82 (s, 1H, CH), 1.79 (s, 3H, CH ). C NMR
2
3
(
125 MHz, DMSO-d ): δ = 161.5, 152.2, 146.8, 136.3, 132.0, 129.2, 124.3, 120.8, 97.0, 78.4, 36.3,
6
1
0.1.
In conclusion, we report the synthesis and characterization of a Fe O @Ag-β-CD composite as an
3
4
effective, reusable and environmentally friendly catalyst for the one-pot synthesis of 3,4-
dihydropyrimidinone and 1,4-dihydroprano[2,3-c]pyrazole derivatives in aqueous medium with good
1
5