Uses
1,10-Phenanthroline-5,6-dione is a Bifunctional quinone oxidant which, when used in conjunction with Zn2+ catalysts, is used to affect the aerobic oxidation of secondary amines to a variety of value added motifs, including indoles.
General Description
1,10-Phenanthroline-5,6-dione (phendio) forms Cu(II) and Ag(I) phendio complexes, which show potent anti-fungal and anti-cancer activity. The modification of glassy carbon (GC) electrodes with phendio complexes of transition metals leads to the catalytic oxidation of NADH at low overpotential.
Synthesis
1. Add 35 mL of concentrated H2SO4 to a 250 mL three-necked flask at 0 °C. 2.
2. 1,10-phenanthroline (2.5 g, 28 mmol) was added slowly to the three-necked flask.
3. KBr (5 g, 42 mmol) and HNO3 (17.5 mL) were added sequentially at 5 °C.
4. Stir the reaction mixture at room temperature for 20 minutes.
5. Warm the reaction system to 130 °C and hold for 2 hours.
6. Slowly pour the hot yellow reaction solution into 150 g of ice water.
7. Neutralize to pH=7 with Na2CO3.
8. Extract the reaction mixture with CHCl3.
9. Combine the organic phases and dry with anhydrous Na2SO4.
10. Concentrate the organic phase under pressure.
11. purify the crude product by recrystallization from anhydrous ethanol to give 2.4 g (96% yield) of 1,10-phenanthroline-5,6-dione.
References
[1] Dalton Transactions, 2016, vol. 45, # 41, p. 16366 - 16378
[2] Chemistry - A European Journal, 2012, vol. 18, # 50, p. 16061 - 16072
[3] Russian Journal of Organic Chemistry, 2005, vol. 41, # 11, p. 1690 - 1693
[4] Journal of the American Chemical Society,
[5] Journal of the American Chemical Society, 2009, vol. 131, p. 4 - 5
