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General procedure: A dry 50?mL flask was charged with 2-aminobenzamides 1 (2.1?mmol), 5,5-dimethyl-1,3-cyclohexanedione 2 (1.0?mmol), iodine (0.026?g, 0.01?mmol) and toluene (10.0?mL). The mixture was stirred at reflux until the reactant 1 was consumed. After the completion of the reaction monitored by TLC, toluene was recovered by distillation under reduced pressure, and the residue was purified by silica column chromatography using ethyl acetate and petroleum ether (1:3) as the eluent to give products 3.#10;
2-methoxy-12-methyl-12,13-dihydropyrazolo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79%
With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 12h;
General procedure: A 25-mL flask was charged with o-halogenated benzaldehyde 1 (1.0mmol), 1H-indazol-6-amine 2 (133 mg, 1.0 mmol), cyclohexane-1,3-dione 3 (1.0 mmol), CuI (10 mg, 0.05 mmol), Cs2CO3 (652 mg, 2.0mmol), and DMSO (10 mL). The mixture was stirred at reflux untilcompletion (TLC monitoring). The solid was filtered off, and the filtratewas distilled under reduced pressure to recover the solvent; theresidue was purified by chromatography (silica gel, EtOAc-petroleumether, 1:2) to give 4.