73% |
With copper; Selectfluor In acetonitrile at 80℃; for 24h; |
1 Example 1
0.30 mmol of N-formyl-o-phenylaniline (59.1 mg), 0.03 mmol of copper powder (1.8 mg), 0.6 mmolSelectfluor (212.4 mg) was sequentially added to a 15 mL pressure-resistant sealed container, followed by the addition of 3 mL of acetonitrile.The mixture was heated in an oil bath at 80 ° C, detected by TLC, and the reaction was completed in 24 hours. After cooling to room temperature, the reaction mixture was diluted with 10 mL of dichloromethane and filtered to give a clear liquid.After evaporating the solvent, it was separated by column chromatography (a mixture of petroleum ether/ethyl acetate 30:1 as eluent).The eluent containing the desired product was evaporated to remove the solvent to afford 42.7 mg (yield: 73%) of pale yellow solid phenanthridone. |
73% |
With water; copper; Selectfluor In acetonitrile at 80℃; for 12h; |
4.5. Typical experimental procedure for the synthesis of phenanthridinones 8 from 7
General procedure: The starting material N-(20-arylphenyl)formamide 7 were synthesized according to the literature procedures [21]. 7 (0.3 mmol), Cu(0) powder (1.92 mg, 10 mol %), Selectfluor (212.6 mg, 0.6 mmol, 2 equiv), and MeCN (water content: 0.05 w/w %, 3 mL) were added to a 25-mL flask. Then the reaction mixture was stirred at 80 °C for 12 h. Upon completion, the resulting mixture was diluted with CH2Cl2 (10 mL) and filtered through Celite. After evaporation of the solvent under vacuum, the residue was purified by column chromatography on silica gel (100-200 mesh) using petroleum ether-EtOAc (20/1, V/V) as eluent to give pure 8. 4.5.1. Phenanthridin-6(5H)-one (8a)[22] Purification by column chromatography (petroleum ether/EtOAc, 20/1) as white solid (42.7 mg, 73%); m.p. 128-130 °C (lit. [22] m.p. 198 °C); IR (neat): ν = 1702 (C=O) cm-1; 1H NMR (CDCl3, 500 MHz): δ 9.60 (s, 1H), 8.56 (d, J = 6.0 Hz, 1H), 7.92 (d, J = 7.5 Hz, 2H), 7.65-7.36 (m, 5H); 13C NMR (CDCl3, 125 MHz): δ 157.3, 137.6, 137.0, 127.7, 126.9, 126.0 (2C), 124.6, 124.2, 120.6, 119.7, 116.7, 109.8. |