Elsevier

Tetrahedron Letters

Volume 43, Issue 8, 18 February 2002, Pages 1397-1399
Tetrahedron Letters

Lower primary alkanols and their esters in a Ritter-type reaction with nitriles. An efficient method for obtaining N-primary-alkyl amides

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Abstract

N-Primary-alkyl amides RCONHR1 were obtained by a Ritter-type reaction of nitriles RCN with lower primary alkanols R1OH or their esters in the presence of acids.

N-primary-alkyl amides were obtained by a Ritter-type reaction of nitriles with lower primary alkanols or their esters in the presence of acids.

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    The Ritter reaction, the reaction of nitrile with a substituted alkene or alcohols using an acid catalyst, is a method of choice for the production of amides, which are versatile intermediates in organic synthesis [25–27]. Due to its potential importance, remarkable progress has been made in the field of catalytic Ritter-type reactions with the betterment in terms of milder reaction conditions, better catalysts, substrate diversities, increased yields etc, like acid catalyzed methods [28–31], solid supported-acid catalysts [32,33], triflamides [34], Nafion-H [35] and many others catalyzed methods [36–39]. On the other hand, various modified versions of this reaction have been reported for Ritter-type reaction by relatively stable in situ-generated carbocations from, esters, alkenes, alcohols, ethers, silyl ethers, alkylborons and carbonium salts [37,40–43] by using heterogeneous and homogeneous acidic catalysts.

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