AN APPLICATION OF PHOSPHONIUM SALTS FOR THE NEW UNSATURATED AMIDES SYNTHESIS
DOI:
https://doi.org/10.32782/naturaljournal.11.2025.38Keywords:
alkylidenephosphorane, phosphonium salt, amid, Wittig reactionAbstract
An interaction of phosphonium salts containing amide group with aromatic aldehydes have been investigated. The possibility of application of the Wittig reaction between aldehydes and alkylidenephosphoranes, formed in the interaction of the corresponding phosphonium salts with bases as a method for obtaining of new amides of the unsaturated acids have been studied. This class of substances is important due to the wide spectrum of their biological activity – insecticidal, antifungal, antibacterial and acaricidal activity, antitumor, antispasmodic action, etc. The obtained compounds also seem to be promising intermediates for obtaining various nitrogen- and oxygen-containing heterocycles: lactams, lactones, oxazolines, etc. A number of phosphonium salts containing N-alkyl and N-aryl substituted amide groups have been obtained by the interactionof triphenylphosphine with amides of chloro- and bromoacetic acids. The obtained salts have been put into reaction with various aromatic aldehydes; the conditions and features of the Wittig reaction for amide-containing phosphonium salts depending on the temperature, environment, etc. have been studied. It was shown that the reaction is a promising method for the synthesis of unsaturated amides. Its advantages are the ease of product formation, low temperature and, in general, mild conditions, particularly there is no need to use caustic alkalis as bases. That makes possibleto use in the reaction complex aldehydes, particularly those containing ester groups, withoutthe risk of their hydrolysis. Another advantage of the method is the possibility of carrying outthe synthesis in one stage, without isolating of the intermediate products – alkylidenephosphoranes in an individual state. The developed technique made possible to obtain a number of unsaturated aliphatic-aromatic amides containing structural fragments of interest for their potential physiological activity – fragments of anestezin, isonicotinic acid, etc.
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