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Synthesis 2013; 45(10): 1357-1363
DOI: 10.1055/s-0033-1338413
DOI: 10.1055/s-0033-1338413
paper
Synthesis of Unsymmetrical 2-Pyridyl Ureas via Selenium-Catalyzed Oxidative Carbonylation of 2-Aminopyridine with Aromatic Amines
Further Information
Publication History
Received: 27 January 2013
Accepted after revision: 21 March 2013
Publication Date:
25 April 2013 (online)
Abstract
A simple, one-pot, phosgene-free approach to a series of unsymmetrical 2-pyridyl ureas starting from 2-aminopyridine and various aromatic amines is reported for the first time. The procedure employs inexpensive selenium as the catalyst, and carbon monoxide (instead of phosgene) as the carbonyl reagent. The products are obtained in moderate to good yields via selenium-catalyzed oxidative cross-carbonylation of the substrate amines in the presence of oxygen. The selenium functions as a phase-transfer catalyst and can be recovered easily and reused without any significant degradation of its catalytic activity.
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