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. 2019 Apr 25;9(23):12801–12812. doi: 10.1039/c9ra01679a

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 graphic file with name c9ra01679a-u32.jpg graphic file with name c9ra01679a-u33.jpg 17 91 232–234 234–23549
2 6b graphic file with name c9ra01679a-u34.jpg graphic file with name c9ra01679a-u35.jpg 15 94 216–219 214–21623
3 6c graphic file with name c9ra01679a-u36.jpg graphic file with name c9ra01679a-u37.jpg 15 92 180–182 179–18025
4 6d graphic file with name c9ra01679a-u38.jpg graphic file with name c9ra01679a-u39.jpg 15 95 207–210 198–20024
5 6e graphic file with name c9ra01679a-u40.jpg graphic file with name c9ra01679a-u41.jpg 15 93 212–214 215–21723
6 6f graphic file with name c9ra01679a-u42.jpg graphic file with name c9ra01679a-u43.jpg 20 94 229–231 228–23032
7 6g graphic file with name c9ra01679a-u44.jpg graphic file with name c9ra01679a-u45.jpg 15 92 208–211 207–20952
8 6h graphic file with name c9ra01679a-u46.jpg graphic file with name c9ra01679a-u47.jpg 15 95 207–209 210–21149
9 6i graphic file with name c9ra01679a-u48.jpg graphic file with name c9ra01679a-u49.jpg 15 92 225–229 227–23052
10 6j graphic file with name c9ra01679a-u50.jpg graphic file with name c9ra01679a-u51.jpg 25 91 217–220 220–22250
11 6k graphic file with name c9ra01679a-u52.jpg graphic file with name c9ra01679a-u53.jpg 25 90 203–205 201–20249
12 6l graphic file with name c9ra01679a-u54.jpg graphic file with name c9ra01679a-u55.jpg 20 92 223–225 224–22659
13 6m graphic file with name c9ra01679a-u56.jpg graphic file with name c9ra01679a-u57.jpg 25 94 237–239 238–24051
14 6n graphic file with name c9ra01679a-u58.jpg graphic file with name c9ra01679a-u59.jpg 20 92 209–211 210–21226
a

Reaction conditions: dimedone (1 mmol), aldehyde (1 mmol), malononitrile (1.1 mmol), MNPs@Cu (10 mg).

b

The yields refer to Isolated products.