Unprecedented Intermolecular Transamidation Reaction of N-Carbamoylmethyl-N'-tosylguanidines

N-Carbamoylmethyl-N‘-tosyl guanidine 2 reacts easily with primary alkylamines to afford substituted carboxamides 3. The reaction proceeds via a five-membered-ring intermediate 5, which could be isolated, and features a rare example of an intermolecular transamidation reaction under mild conditions....

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Bibliographic Details
Published in:Organic letters 2003-10, Vol.5 (21), p.3851-3853
Main Authors: Lasri, Jamal, González-Rosende, M. Eugenia, Sepúlveda-Arques, José
Format: Article
Language:English
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Summary:N-Carbamoylmethyl-N‘-tosyl guanidine 2 reacts easily with primary alkylamines to afford substituted carboxamides 3. The reaction proceeds via a five-membered-ring intermediate 5, which could be isolated, and features a rare example of an intermolecular transamidation reaction under mild conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035377z