Propargyl alcohol → Pirquinozol

Participants

Reaction Steps

4.8 g (0.03 mole) of 3-diazooxindole is suspended in 500 ml of benzene and 1.96 g (0.033 mole) of propargyl alcohol added. The reaction mixture is refluxed overnight under nitrogen, after which 19.6 g (0.33 mole) of propargyl alcohol is added and the reaction continued under reflux for a total of 48 hours. The tan solid which precipitates is filtered off (1.5 g, 23% yield), m.p. 272°-275° (sl. dec.). Recrystallization from methanol gives crystals of the title compound, m.p. 286°-288° (sl. dec.).

Provenance & Evidence