1313358-10-9Relevant academic research and scientific papers
Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds: modular and regiocontrolled synthesis of multisubstituted pyrroles
Tan, Wei Wen,Yoshikai, Naohiko
, p. 6448 - 6455 (2015)
In the presence of a copper(ii) catalyst, enolizable imines bearing various N-substituents and α-diazo-β-ketoesters undergo denitrogenative and dehydrative condensation to afford highly substituted pyrroles in moderate to good yields with exclusive regioselectivity. The reaction likely involves nucleophilic addition of the imine nitrogen to a copper carbenoid, tautomerization of the resulting azomethine ylide to an α-enaminoketone, and a subsequent enamine-ketone cyclocondensation. With Yb(OTf)3 as a unique cocatalyst, α-diazo-β-diketones also participate in the same condensation reaction. The present reaction is applicable to acyclic, exocyclic, and endocyclic imines with tolerance of a broad range of functional groups and heterocyclic moieties, thus opening a new convenient route for the synthesis of the lamellarin family of natural products.
Polyethylene glycol (PEG-400) as an efficient and recyclable reaction medium for one-pot synthesis of polysubstituted pyrroles under catalyst-free conditions
Nagarapu, Lingaiah,Mallepalli, Raghu,Yeramanchi, Lingappa,Bantu, Rajashaker
experimental part, p. 3401 - 3404 (2011/06/28)
Polyethylene glycol (PEG) was found to be an inexpensive non-toxic and effective medium for the one-pot synthesis of highly functionalized pyrroles. Utilizing this protocol various pyrrole derivatives were synthesized in excellent yields. Environmental acceptability, low cost, high yields, and recyclability of the PEG are the important features of this protocol.
