Table 3.
Preparation of 4H-pyrans derivatives by using Cu2(NH2-BDC)2(DABCO) as the catalysta
.
Entry | Aldehyde | Product | Time (min) | Yield (%)b | M.P. (°C) | M.P. (°C) [Lit.] |
---|---|---|---|---|---|---|
1 | 4-Chloro benzaldehyde | 8a | 22 | 92 | 160–163 | 162 [55] |
2 | 2-Chloro benzaldehyde | 8b | 25 | 90 | 188–192 | 190-191 [56] |
3 | 4-Bromo benzaldehyde | 8c | 25 | 92 | 179–182 | 179-180 [57] |
4 | Benzaldehyde | 8d | 60 | 80 | 185–188 | 189 [58] |
5 | 2-Nitro benzaldehyde | 8e | 42 | 90 | 178–180 | 177-178 [57] |
6 | 3-Nitro benzaldehyde | 8f | 40 | 87 | 186–190 | 187-188 [57] |
7 | 4-Nitro benzaldehyde | 8g | 40 | 89 | 175–178 | 174-176 [59] |
8 | 4-Methyl benzaldehyde | 8h | 18 | 90 | 173–176 | 175-176 [59] |
9 | 4-Chloro benzaldehyde | 9a | 30 | 65 | 149–154 | 153-155 [60] |
10 | 3-Nitro benzaldehyde | 9b | 42 | 63 | 160–164 | 166 [61] |
Reaction conditions: aldehyde (2, 1.0 mmol), malononitrile (3, 1.0 mmol), acetyl acetone or ethyl acetoacetate (7a-b, 1.0 mmol), Cu2(NH2-BDC)2(DABCO) (0.04 g), solvent-free and room Temperature.
Isolated yield.