ANO-catalyzed multicomponent synthesis of 3-nitroalkyl-N-substituted pyrroles

A sustainable and atom-economic method was developed to prepare functionalized nitroalkyl pyrroles through a multicomponent reaction involving anilines, hexane-2,5-dione, and β-nitrostyrene derivatives. Ammonium niobium oxalate (ANO) was used as a cheap and reusable catalyst with ethanol as an eco-f...

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Bibliographic Details
Main Authors: Luiz H. Dapper, Viviane T. Mena, Márcio S. Silva, Filipe Penteado, Eder J. Lenardão
Format: Article
Language:English
Published: Elsevier 2025-06-01
Series:Tetrahedron Green Chem
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Online Access:http://www.sciencedirect.com/science/article/pii/S2773223124000256
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Summary:A sustainable and atom-economic method was developed to prepare functionalized nitroalkyl pyrroles through a multicomponent reaction involving anilines, hexane-2,5-dione, and β-nitrostyrene derivatives. Ammonium niobium oxalate (ANO) was used as a cheap and reusable catalyst with ethanol as an eco-friendly solvent. A total of twenty-five N-substituted nitroalkyl-functionalized pyrroles were prepared in moderate to excellent yields (up to 93%). The method was successfully applied to electron-rich and electron-poor anilines, as well as to butylamine, simply by using a telescoping procedure (one-pot). Besides, the easy transformation of the obtained product in a primary amine was demonstrated.
ISSN:2773-2231