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

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.

SUBMITTER: Phakhodee W

PROVIDER: S-EPMC9090163 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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

Phakhodee Wong W Duangkamol Chuthamat C Wiriya Nitaya N Pattarawarapan Mookda M

RSC advances 20181114 67

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 synth ...[more]

PMID: 35559089

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