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. 2022 Aug 9;12(34):22004–22019. doi: 10.1039/d2ra03312g

Synthesis of podophyllotoxin-naphthoquinone compounds via microwave-assisted three-component reactionsa.

graphic file with name d2ra03312g-u1.jpg
Entry Product Ar Time (min) Yieldb (%) Mpc (°C)
1 5a 3-OMePh 15 86 290–293d
2 5b 3-BrPh 15 83 328–329d
3 5c 3-NO2Ph 15 75 283–285d
4 5d Ph 15 84 329–334d
5 5e 4-MePh 15 88 320–322d
6 5f 2-NO2Ph 15 73 289–292d
7 5g 3-Oxo-1,3-dihydro benzofuran-5-yl 15 85 295–296d
8 5h 2-OHPh 20 80 311–312
9 5i 4-OHPh 20 79 304–305
10 5j 4-NO2Ph 15 82 298–299
11 5k 4-CNPh 15 89 306–307
12 5l 3,4-(MeO)2Ph 15 85 288–289
13 5m 3,4,5-(MeO)3Ph 15 86 310–311
14 5n Pyridin-3-yl 15 81 210–212
15 5o 5-Br-pyridin-2-yl 15 83 274–275
a

All the reactions were carried out in 1 mmol scale in 3 mL solvent at 120 °C under MW at the maximum power of 150 W, and the ratio of 6/2/3 was 1/1/1.

b

Isolated yields.

c

Decomposed.

d

These results were reported in our previous study.46