O-Iodoxybenzoic acid (IBX): A versatile reagent for the synthesis of N-substituted pyrroles mediated by β-cyclodextrin in water

Tetrahedron Letters

Volumn 52, Issue 34, 2011, Pages 4481-4484

  Narayana Murthy, S ^a   Nageswar, Y V D ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; BETA CYCLODEXTRIN; HETEROCYCLIC COMPOUND; IODOXYBENZOIC ACID; PYRROLE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG; WATER;

AROMATIZATION; ARTICLE; ENERGY YIELD; ROOM TEMPERATURE; SYNTHESIS;

EID: 79960840059     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.077     Document Type: Article

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44. General procedure for the synthesis of N-benzylpyrroles. To an aqueous solution of β-cyclodextrin (1.0 mmol of β-CD in 5 mL of water), IBX (2.0 mmol), N-benzylpyrrolidine (1.0 mmol) was added while stirring, and stirring was continued for the stipulated reaction time as shown in the Table at room temperature. After completion of reaction as indicated by TLC, the reaction mixture was extracted with ethyl acetate (3 × 5 mL), the combined organic layers were washed with saturated brine solution, dried and concentrated in vacuum. The crude product was purified by column chromatography on Silica gel using hexane/ethyl acetate (9:1) as an eluent.
45. 3; TMS) 14.37, 50.59, 60.27, 109.90, 111.85, 113.31, 126.08, 126.39, 127.71, 128.81, 129.05, 131.96, 137.22, 167.29.