MNPs@Cu-catalyzed synthesis of 2-amino-3-cyano-pyrano[3,2-c] chromen-5(4H)-one (4) derivativesa.
Entry | Product | RCHO (2) | Product | Time (min) | Yield (%)b | MP (obsd) (°C) | MP (lit.) (°C) |
---|---|---|---|---|---|---|---|
1 | 4a | 12 | 91 | 258–260 | 256–25817 | ||
2 | 4b | 12 | 92 | 260–263 | 260–26219 | ||
3 | 4c | 8 | 94 | 249–251 | 250–25219 | ||
4 | 4d | 8 | 94 | 243–245 | 244–24618 | ||
5 | 4e | 8 | 95 | 262–264 | 263–26548 | ||
6 | 4f | 8 | 95 | 259–261 | 260–26217 | ||
7 | 4g | 15 | 92 | 233–235 | 236–23853 | ||
8 | 4h | 20 | 90 | 240–243 | 242–24446 | ||
9 | 4i | 15 | 93 | 222–224 | 221–22318 | ||
10 | 4j | 20 | 90 | 226–229 | 228–23017 | ||
11 | 4k | 15 | 92 | 256–259 | 253–25447 | ||
12 | 4l | 15 | 90 | 261–264 | 260–26217 | ||
13 | 4m | 15 | 90 | 250–252 | 252–25417 | ||
14 | 4n | 15 | 95 | 258–260 | 259–26142 | ||
15 | 4o | 20 | 89 | 261–264 | 265–26717 |
Reaction conditions: 4-hydroxycoumarin (1 mmol), aldehyde (1 mmol), malononitrile (1.1 mmol), MNPs@Cu (10 mg).