Facile Synthesis of Hydroxyformamidines by the N-Oxidation of Their Corresponding Formamidines

The N-oxidation of N, N'-disubstituted amidines with MCPBA (m-chloroperoxibenzoic acid) affords a mild, rapid, and efficient route to the corresponding hydroxyamidines This novel synthetic route for the preparation of N, N'-disubstituted hydroxyamidines provides an attractive alternative t...

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Bibliographic Details
Published inSynlett no. 3; pp. 405 - 409
Main Authors Cibian, Mihaela, Langis-Barsetti, Sophie, Hanan, Garry S.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.02.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
N-oxidation
LIGANDS
MCPBA
COMPLEXES
SPECTROPHOTOMETRIC DETERMINATION
hydroxyformamidines
peroxides
substituent effects
CATALYSTS
formamidines
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Summary:The N-oxidation of N, N'-disubstituted amidines with MCPBA (m-chloroperoxibenzoic acid) affords a mild, rapid, and efficient route to the corresponding hydroxyamidines This novel synthetic route for the preparation of N, N'-disubstituted hydroxyamidines provides an attractive alternative to the classical one. It was found that the efficiency of the N-oxidation reaction, and the stability of the hydroxyformamidines are influenced by the substitution on the N, N'-diaryl rings, for example, higher yields (up to 92%) and more stable products are obtained for the compounds bearing substituents in the 2,6-positions of the phenyl rings. H-1 NMR and C-13 NMR, HRMS and/or elemental analysis were used to characterize the products.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0030-1259329