Recyclable, Graphite-Catalyzed, Four-Component Synthesis of Functionalized Pyrroles

A facile, convenient, and multicomponent coupling strategy for the synthesis of highly functionalized pyrroles is developed using graphite as a catalyst, but devoid of moisture-sensitive metal catalysts and corrosive acidic reagents. This method involves four-component coupling reactions of ethyl ac...

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Bibliographic Details
Published in:Synthetic communications 2014-04, Vol.44 (8), p.1103-1110
Main Authors: Nandeesh, K. N., Raghavendra, G. M., Revanna, C. N., Jenifer Vijay, T. A., Rangappa, K. S., Mantelingu, K.
Format: Article
Language:English
Subjects:
Carbon catalyst
graphite
multicomponent reaction
Paal-Knorr synthesis
pyrroles
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Summary:A facile, convenient, and multicomponent coupling strategy for the synthesis of highly functionalized pyrroles is developed using graphite as a catalyst, but devoid of moisture-sensitive metal catalysts and corrosive acidic reagents. This method involves four-component coupling reactions of ethyl acetoacetate compound or diethyl acetylene dicarboxylate, amines, aromatic aldehydes, and nitromethane without an inert atmosphere. This approach provides easy access to highly substituted pyrroles in good yields via one-pot tandem reaction. The method is very simple, straightforward, and environmentally friendly compared to the existing methods. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2013.848368