NAVIGATION
Zhang, Qianqian, et al. Organic Chemistry Frontiers, 2018, 5, 1, 80-87.
Cesium carbonate (Cs2CO3)-mediated cascade reaction can be used to synthesize dihydropyrrozinyl[3,2-b ]indol-10-one. The reaction mechanism involves sequential nucleophilic attacks of DMF with the enolate and pyrrolyl nitrogen, followed by the formation of transition metal-free C-N bonds.
Cesium carbonate-mediated cascade reaction procedure
· A sealed tube was charged with 2-(2-bromophenyl)-1-(N-tosyl-2-pyrrolyl)propan-1-one (1.0 mmol), Cs2CO3 (2.0 mmol) and DMF (10 mL).
· The reaction system was recharged with nitrogen three times. The reaction mixture was heated at 120 °C for 24 h and cooled.
· The mixture was partitioned between EtOAc (20 mL) and H2O (40 mL). The separated aqueous phase was extracted with EtOAc (3 × 20 mL).
· The combined organic extracts were washed with brine (100 mL), then dried (Na2SO4), filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc) to afford the products.
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