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Synlett

Volumn , Issue 17, 2007, Pages 2699-2702

A mild and effective method to synthesize carbazolones by CuI/L-proline-catalyzed intramolecular arylation

(4) Yan, Shaoyu a Wu, Haihong a Wu, Nan a Jiang, Yongwen a

a EAST CHINA NORMAL UNIVERSITY (China)

Author keywords

2 iodoaryl enaminone; Catalysis; Intramolecular cross coupling; L proline

Indexed keywords

3,4 DIHYDROCYCLO PENTAL INDOLE 1 ONE DERIVATIVE; ANILINE DERIVATIVE; CARBAZOL 4 ONE DERIVATIVE; CARBAZOLE DERIVATIVE; COPPER IODIDE; DIMETHYL SULFOXIDE; ENAMINE; KETONE DERIVATIVE; N 2 IODO ENAMINONE DERIVATIVE; POTASSIUM CARBONATE; POTASSIUM HYDROXIDE; PROLINE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; SYNTHESIS;

EID: 35648999046 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-991079 Document Type: Article

Times cited : (26)

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- Typical Experimental Procedure for the Synthesis of N-2-Iodoaryl Enaminone 4 A mixture of 2-iodobenzenamine (2.18 g, 10 mmol, 1,3-cyclohexanedione (1.12 g, 10 mmol, and TsOH·H 2O (190 mg, 1 mmol) in 30 mL of toluene was refluxed for 6 h. The cooled mixture was washed with H2O and brine and was dried over Na2SO4. After removal of the solvent in vacuum, the residue was chromatographed on silica gel using PE-EtOAc (1:1) as the eluent to afford 3-(2′-iodophenylamino)cyclohex-2-enone (4a, 2.63 g, 84, Synthesis of Carbazol-4-one 3 A mixture of 3-(2′-iodophenylamino) cyclohex-2-enone (4a, 313 mg, 1 mmol, CuI, 19 mg, 0.1 mmol, L-proline (23 mg, 0.2 mmol, and KOH (224 mg, 4 mmol) in 4 mL of DMSO was heated at 90°C under nitrogen atmosphere for 24 h. The cooled solution was poured into H2O and extracted with EtOAc. The combined organic layers were washed with
- 4. After removal of the solvent in vacuum, the residue was chromatographed on silica gel using PE-EtOAc (1:1) as the eluent to afford tetrahydrocarbazol-4-one (3a, 170 mg, 92%).

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