Lower primary alkanols and their esters in a Ritter-type reaction with nitriles. An efficient method for obtaining N-primary-alkyl amides
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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2020, PolyhedronCitation Excerpt :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.
Microwave assisted, Ca(II)-catalyzed Ritter reaction for the green synthesis of amides
2014, Tetrahedron LettersPreparation of imidazolines from aziridines and nitriles via TfOH promoted Ritter process
2014, Chinese Chemical LettersCitation Excerpt :For example in reference [7f], InCl3, ErCl3 and YbCl3 do not give any Ritter products, but deliver chlorinated compounds as the major product, while Et3OBF4 results in some fluorinated product [7b] accompanied with the imidazoline. Furthermore, the imidazolines could be easily hydrolyzed to diamine derivatives with the promotion of HCl in EtOH in very high yield [8]. Considering the important application of diamines, the efficient preparation of imidazolines is of potential and high demand.
Ritter-Type Reactions
2014, Comprehensive Organic Synthesis: Second Edition