6533b7d8fe1ef96bd12697d3

RESEARCH PRODUCT

ChemInform Abstract: Preparation of N,O-Aminals as Synthetic Equivalents of H2C=NAr and (H2C=NHAr)+ Ions: Neutral- and Acid-Promoted Transformations.

José BarluengaElena Gonzalez-nuñezPedro J. CamposAna M. BayónGregorio AsensioYolanda MolinaYolanda Molina

subject

chemistry.chemical_compoundPrimary (chemistry)EquivalentGeneral purposeChemistrySodium cyanoborohydridePh controlReactivity (chemistry)General MedicineMedicinal chemistryMethaneIon

description

A general method for the synthesis of N,O-aminals derived from primary aromatic amines is described. The reactivity of these compounds under neutral and acidic conditions has been studied and the title compounds can be envisaged as general purpose H2CNAr or (H2CNHAr)+ equivalents. N,O-Aminals have been converted into perhydrotriazines by moderate heating and into bis(4-aminoaryl)methane derivatives or N-benzylarylamines, respectively when heated in acidic media with pH control. Reduction of N,O-acetals with sodium cyanoborohydride has revealed that the C–O bond is broken exclusively in acidic media.

https://doi.org/10.1002/chin.198843152