MNPs@Cu-catalyzed synthesis of 2-amino-3-cyano-7,8-dihydro-4H-chromen-5(6H)-one (6)derivativesa.
Entry | Product | RCHO (2) | Product | Time (min) | Yield (%)b | MP (obsd) (°C) | MP (lit.) (°C) |
---|---|---|---|---|---|---|---|
1 | 6a | 17 | 91 | 232–234 | 234–23549 | ||
2 | 6b | 15 | 94 | 216–219 | 214–21623 | ||
3 | 6c | 15 | 92 | 180–182 | 179–18025 | ||
4 | 6d | 15 | 95 | 207–210 | 198–20024 | ||
5 | 6e | 15 | 93 | 212–214 | 215–21723 | ||
6 | 6f | 20 | 94 | 229–231 | 228–23032 | ||
7 | 6g | 15 | 92 | 208–211 | 207–20952 | ||
8 | 6h | 15 | 95 | 207–209 | 210–21149 | ||
9 | 6i | 15 | 92 | 225–229 | 227–23052 | ||
10 | 6j | 25 | 91 | 217–220 | 220–22250 | ||
11 | 6k | 25 | 90 | 203–205 | 201–20249 | ||
12 | 6l | 20 | 92 | 223–225 | 224–22659 | ||
13 | 6m | 25 | 94 | 237–239 | 238–24051 | ||
14 | 6n | 20 | 92 | 209–211 | 210–21226 |
Reaction conditions: dimedone (1 mmol), aldehyde (1 mmol), malononitrile (1.1 mmol), MNPs@Cu (10 mg).
The yields refer to Isolated products.