A convenient one-pot synthesis of N-substituted amidoximes and their application toward 1,2,4-oxadiazol-5-ones?

RSC Advances Pub Date: 2018-11-14 DOI: 10.1039/C8RA08207C

Abstract

The first direct one-pot approach for the synthesis of N-substituted amidoximes from secondary amides or the intermediate amides has been developed. Through the Ph3P–I2-mediated dehydrative condensation, a variety of N-aryl and N-alkyl amidoximes (R1(C[double bond, length as m-dash]NOH)NHR2, where R1 or R2 = aryl, alkyl, or benzyl) were readily afforded under mild conditions and short reaction times. The synthetic application of the obtained amidoximes has also been demonstrated through the formation of 1,2,4-oxadiazolones via base-mediated carbonylative cyclization with 1,1′-carbonyldiimidazole.

Graphical abstract: A convenient one-pot synthesis of N-substituted amidoximes and their application toward 1,2,4-oxadiazol-5-ones
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