Diethyl Ether → Furo[2,3-c]isoquinolin-5(4H)-one

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (1 ml) was added to a suspension of 3-phenyl-2-furancarboxylic acid (300 mg, 1.46 mmol) in 10 ml of dry benzene and the mixture was refluxed for 2 hours. The solvent and the excess of thionyl chloride were removed under reduced pressure, the residue was taken up using 10 ml of dry THF and cooled to 0° C. Sodium azide (1.5 mmol) dissolved in the minimal amount of water was quickly added and the resulting solution was stirred for 1 hour at room temperature. After pouring into 100 ml of cracked ice/H2O and extraction with diethyl ether (4×100 ml), and the collected organic layers were dried over Na2SO4. The filtrate was gently evaporated under reduced pressure, the residue was dissolved in 10 ml of o-dichlorobenzene, and the resulting mixture was refluxed for 5-10 hours. The mixture was then cooled, and directly submitted to the flash chromatography, elution with dichloromethane/methanol (99/1) afforded to the title compound. Yield: 68%.

Provenance & Evidence