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General Procedure
for Pyranopyrazoles: To a stirred mixture of hydrazine hydrate 1 (2 mmol) and ethyl acetoacetate 3 (2 mmol), aldehyde 2 (2
mmol) and malononitrile 4 (2 mmol) were
added successively at r.t. with vigorous stirring for 3-11
min. The precipitated solid was filtered, and washed with a mixture
of EtOAc-hexane (20:80). The product obtained was pure
as found in TLC and ¹H NMR and ¹³C
NMR spectroscopy. However, the products were further purified by
recrystallization from EtOAc. Table
[¹]
,
entry 4: yellow solid; mp 158-161 ˚C. ¹H
NMR (500 MHz, DMSO-d
6): δ = 1.75
(s, 3 H), 2.16 (s, 3 H), 2.46 (s, 2 H), 4.53 (s, 1 H), 6.85 (s,
1 H), 7.01 (d, 1 H, J = 12.0 Hz),
7.03 (d, 1 H, J = 8.4 Hz), 12.09
(br s, 1 H). ¹³C NMR (125 MHz, DMSO-d
6): δ = 10.3,
14.8, 39.8, 57.7, 98.1, 115.2, 121.3, 127.2, 130.9, 136.2, 140.9,
155.2, 159.0, 161.3. IR (KBr): 3484.5, 3239.7, 2195.3, 1638.0, 1597.6, 1493.4,
1399.4, 1116.5, 1057.3, 822.1, 749.0, 549.6 cm-¹. LCQ-MS
(ESI): m/z calcd
for C15H13FN4O: 284.0; found: 284.3.
Anal. Calcd for C15H13FN4O: C,
63.37; H, 4.61; N, 19.71. Found: C, 6 3.29; H, 4.52; N, 19.63.
15 Table
[¹]
,
entry 10: yellow solid; mp 145-147 ˚C. ¹H
NMR (500 MHz, DMSO-d
6): δ = 1.76
(s, 3 H), 2.47 (s, 2 H), 4.58 (s, 1 H), 7.10 (d, 2 H, J = 10.0 Hz), 7.47 (d, 2 H, J = 10.0 Hz), 12.05 (br s, 1
H). ¹³C NMR (125 MHz, DMSO-d
6): δ = 10.3, 39.8,
57.2, 97.6, 120.3, 121.2, 130.2, 131.9, 136.2, 144.4, 155.2, 161.4.
IR (KBr): 3476.7, 3232.8, 3100.4, 2193.4, 1648.6, 1600.0, 1490.9,
1401.1, 1069.1, 794.8, 749.3, 541.9 cm-¹.
LCQ-MS (ESI): m/z calcd for C14H11FN4O:
270.0; found: 270.1. Anal. Calcd for C14H11FN4O:
C, 62.22; H, 4.10; N, 20.73. Found: C, 62.16; H, 4.22; N, 20.65.
16 Table
[¹]
,
entry 19: yellow solid; mp 168-170 ˚C. ¹H
NMR (500 MHz, DMSO-d
6): δ = 1.75
(s, 3 H), 2.47 (s, 2 H), 3.69 (s, 3 H), 4.50 (s, 1 H), 6.83 (d,
2 H, J = 8.4 Hz), 7.04 (d, 2
H, J = 8.4 Hz), 12.05 (br s,
1 H). ¹³C NMR (125 MHz, DMSO-d
6): δ = 10.3,
35.9, 55.5, 58.1, 98.4, 114.3, 121.4, 129.0, 136.1, 136.9, 155.3,
158.5, 161.2. IR (KBr): 3481.4, 3253.2, 2925.3, 2191.1, 1642.5,
1600.8, 1492.0, 1392.8, 1258.4, 1172.1, 1031.2, 870.0, 804.4, 565.9
cm-¹. LCQ-MS (ESI): m/z calcd
for C15H14N4O2: 282.0;
found: 282.0. Anal. Calcd for C15H14N4O2:
C, 63.82; H, 5.00; N, 19.85. Found: C, 63.71; H, 5.15; N, 19.94.
