Iron(III)-catalyzed four-component coupling reaction of 1,3-dicarbonyl compounds, amines, aldehydes, and nitroalkanes: A simple and direct synthesis of functionalized pyrroles

Journal of Organic Chemistry

Volumn 75, Issue 5, 2010, Pages 1674-1683

  Maiti, Sukhendu ^a   Biswas, Srijit ^a   Jana, Umasish ^a  

^a JADAVPUR UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALTERNATIVE APPROACH; AROMATIC ALDEHYDE; BUILDING BLOCKES; CHEMICAL EQUATIONS; COMPONENT COUPLING; COUPLING REACTION; DICARBONYL COMPOUNDS; DIRECT SYNTHESIS; ENVIRONMENTALLY-FRIENDLY; EXISTING METHOD; FUNCTIONALIZED; GOOD YIELD; INERT ATMOSPHERES; MULTI-COMPONENT COUPLING; NITROALKANES; ONE POT; TANDEM REACTION;

ALDEHYDES; AMINES; CHEMICAL BONDS; COMPLEXATION; IRON COMPOUNDS; PARAFFINS;

SYNTHESIS (CHEMICAL);

1 (2 METHYL 1,4 DIPHENYL 3 PYRROLYL)ETHANONE; 1 [1 (4 BROMOPHENYL) 4 (4 METHOXYPHENYL) 2 METHYL 1H PYRROL 3 YL]ETHANONE; 1 [1 (4 CHLOROPHENYL) 4 (4 METHYLPHENYL) 2 METHYL 1H PYRROL 3 YL]ETHANONE; 1 [1 (4 FLUOROPHENYL) 4 (4 METHOXYPHENYL) 2 METHYL 1H PYRROL 3 YL]ETHANONE; 1 [1 (4 METHOXYPHENYL) 2 METHYL 4 PHENYL 1H PYRROL 3 YL]ETHANONE; 1 [1 BENZYL 2 METHYL 4 (3' NITROBIPHENYL 2 YL) 1H PYRROL 3 YL]ETHANONE; 1 [1 BENZYL 2 METHYL 4 (4 NITROPHENYL) 1H PYRROL 3 YL]ETHANONE; 1 [1 BENZYL 2 METHYL 4 (THIOPHEN 2 YL) 1H PYRROL 3 YL]ETHANONE; 1 [1 BENZYL 4 (4 CHLOROPHENYL) 2 METHYL 1H PYRROL 3 YL]ETHANONE; 1 [1 BENZYL 4 (FURAN 2 YL) 2 METHYL 1H PYRROL 3 YL]ETHANONE; 1 [1 HEXYL 4 (4 METHOXYPHENYL) 2 METHYL 1H PYRROL 3 YL]ETHANONE; 1 [1,4 BIS(4 METHOXYPHENYL) 2 METHYL 1H PYRROL 3 YL]ETHANONE; 1 [4 (2 BROMOPHENYL) 2 METHYL 1 PHENYL 1H PYRROL 3 YL]ETHANONE; 1 [4 (4 CHLOROPHENYL) 1 (4 METHOXYPHENYL) 2 METHYL 1H PYRROL 3 YL]ETHANONE; 1 [4 (4 CHLOROPHENYL) 1 CYCLOHEXYL 2 METHYL 1H PYRROL 3 YL]ETHANONE; 1 [4 (4 CHLOROPHENYL) 1 HEXYL 2 METHYL 1H PYRROL 3 YL]ETHANONE; 1 [4 (4 METHOXYPHENYL) 2 METHYL 1 4 TOLYL 1H PYRROL 3 YL]ETHANONE; 1,3 DICARBONYL COMPOUND; [1 BENZYL 4 (3 BROMOPHENYL) 2 METHYL 1H PYRROL 3 YL](PHENYL)METHANONE; [5 (4 CHLOROPHENYL) 3 (4 METHOXYPHENYL) 2 METHYLCYCLOPENTA 1,4 DIENYL]PHENYL METHANONE; ALDEHYDE; AMINE DERIVATIVE; AROMATIC COMPOUND; CARBONYL DERIVATIVE; FERRIC CHLORIDE; IRON; LEWIS ACID; METHYL 1 BENZYL 4 (4 CYANOPHENYL) 2 METHYL 1H PYRROLE 3 CARBOXYLATE; NITROALKENE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; COUPLING REACTION; SUBSTITUTION REACTION; SYNTHESIS;

ALDEHYDES; ALKANES; AMINES; CATALYSIS; CROSS-LINKING REAGENTS; CRYSTALLOGRAPHY, X-RAY; IRON; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITRO COMPOUNDS; PYRROLES;

EID: 77949289987     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902661y     Document Type: Article

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127. 3 (10 mol%), 60% of the desired product obtained after 7 h of refluxing.
128. Chemical Equation Represented
129. To prove this, an imine was separately prepared from p-methxoyaniline and benzaldehyde, and when a three-component coupling reaction was conducted with this imine, acetylacetone, and nitromethane under anhydrous (argon atmosphere) conditions in the presence of FeCls, no desired product was obtained. However, when the reaction was carried out in the presence of water (2 equiv), the reaction worked and gave the desired product in comparable yield.