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CeO2-catalyzed one-pot selective synthesis of N-alkyl amides from nitriles, amines and water

Paper ID Volume ID Publish Year Pages File Format Full-Text
41154 45879 2012 7 PDF Available
Title
CeO2-catalyzed one-pot selective synthesis of N-alkyl amides from nitriles, amines and water
Abstract

Among 13 kinds of metal oxides, ceria (CeO2) shows the highest catalytic activity for one-pot selective synthesis of the secondary amide from 2-cyanopyridine and n-octylamine as a test reaction. CeO2 acts as a reusable heterogeneous catalyst, and it is effective for the secondary amide formation from various nitriles and amines in high yields (73% to >99%). Pharmacologically important products such as heteroaromatic N-alky amides and morpholine amide are effectively synthesized, indicating that CeO2 can be a practically useful catalyst. A proposed mechanism includes (1) hydration of nitrile to the primary amide and (2) transamidation of the primary amide with amine as the rate-limiting step. This reaction mechanism provides a reason why the present catalytic system gives high selectivity.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (116 K)Download as PowerPoint slideHighlights► First example for one-pot N-alkyl amides synthesis from heteroaromatic nitriles and amines under neutral conditions. ► Commercial CeO2 as the most active catalyst among various metal oxides. ► Effective synthetic method of pharmaceutically important heteroaromatic amides.

Keywords
Cerium oxide; Amides; One-pot synthesis
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CeO2-catalyzed one-pot selective synthesis of N-alkyl amides from nitriles, amines and water
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volumes 417–418, 29 February 2012, Pages 6–12
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
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Full-text PDF Download
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