Pyrrole reacts with arylglyoxal monohydrates and enaminoketones or enaminoesters in alcoholic media in the presence of FeBr 3 as a catalyst to produce 2,5-bis(1H-pyrrol-2-yl)-1H-pyrrole derivatives in high yields as the only product. Reactions are clean and products are isolated by simple filtration.
Key indicatorsSingle-crystal X-ray study T = 293 K Mean (C-C) = 0.002 Å R factor = 0.045 wR factor = 0.113 Data-to-parameter ratio = 13.2 For details of how these key indicators were automatically derived from the article, see
Multi-component reactions (MCRs), especially threecomponent reactions, offer significant advantages over conventional linear-type syntheses, because the combination of the reaction components to generate new products in a single step is easy and economic [12,13].β-Enaminocarbonyls are important compounds used for selective alkylation and acylation of carbonyl compounds and valuable intermediates for the synthesis of biologically active compounds [14][15][16]. These compounds are useful starting points for the preparation of a variety of heterocyclic compounds [17] utilized for synthesis of pharmaceuticals [18] and are building blocks for amino acids [19], peptides [20] or alkaloids [21].Designing of multi-component reactions in water is another attractive area in chemistry, because water is a cheap, safe and an environmentally benign solvent [22].Multi-component reactions of arylglyoxals and enaminocarbonyls in the presence of different nucleophiles have been recently reported for synthesis of polyfunctionalized pyrroles [23][24][25]. However, to the best of our knowledge there are only a few reports on the simple addition of enaminocarbonyl compounds to arylglyoxals [26]. Caballero et al. reported the condensation of N-unsubstituted enaminoesters with phenylglyoxal to afford N-unsubstituted pyrroles. When N-phenyl-enaminoesters were used, they reported obtaining a complex mixture, from which the pyrrolinone derivative was isolated in 30 % yield. The mechanistic studies established the reversibility of the addition reaction between enaminoester and phenylglyoxal to afford the cyclic intermediate dihydroxy pyrrole and product pyrrolinone in reaction conditions [26]. In continuation of our previous studies on the application of arylglyoxals for the synthesis of heterocyclic compounds [27][28][29], here we wish to report a simple addition reaction between arylglyoxal monohydrates and enaminoketones in water as solvent at Abstract An efficient one-pot synthesis of 2H-pyrroline derivatives by a simple reaction of β-enaminocarbonyls with arylglyoxals in water at room temperature is reported. The addition reaction between arylglyoxal derivatives and β-enaminocarbonyls in water afforded 3,4-dihydroxy-2H-pyrrolines after about 10 min stirring at room temperature. When the reaction was done in the presence of aromatic amines, the corresponding 4-amino-5-hydroxy-2H-pyrroline derivatives were obtained in good yields. All reactions were performed in water at room temperature and the products were isolated by simple filtration.
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