0000000000309324
AUTHOR
Ana M. Bayón
ChemInform Abstract: Preparation of N,O-Aminals as Synthetic Equivalents of H2C=NAr and (H2C=NHAr)+ Ions: Neutral- and Acid-Promoted Transformations.
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.
Preparation of N,O-Aminals as Synthetic Equivalents of H2C=NAr and (H2C=NHAr)+ Ions: Neutral and Acid-promoted Transformations
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 H2C=NAr or (H2C=NHAr)+ 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.
A simple and general synthesis of symmetrical and unsymmetrical bis(arylamino)methanes. Reactions of N,O‐acetals with nitrogen bases
Bis(arylamino)methanes 4 free of amine contamination have been efficiently synthesized from N,O-acetals 1 following three different methodologies. The first two are useful for symmetrical aminals and involve the decomposition of an N,O-acetal by a base (phenyllithium or a lithium arylamide) and trapping of the resulting methyleneamine 2 by the equimolar amount of the corresponding arylamine. The third method allows the preparation of either symmetrical or unsymmetrical aminals and consists of decomposing the starting N,O-acetal 1 by heating in vacuo in the presence of the desired arylamine. Ein einfacher und allgemeiner Zugang zu symmetrischen und unsymmetrischen Bis(arylamino)methanen. Rea…
ChemInform Abstract: A Simple and General Synthesis of Symmetrical and Unsymmetrical Bis(arylamino)methanes. Reactions of N,O-Acetals with Nitrogen Bases.
Bis(arylamino)methanes 4 free of amine contamination have been efficiently synthesized from N,O-acetals 1 following three different methodologies. The first two are useful for symmetrical aminals and involve the decomposition of an N,O-acetal by a base (phenyllithium or a lithium arylamide) and trapping of the resulting methyleneamine 2 by the equimolar amount of the corresponding arylamine. The third method allows the preparation of either symmetrical or unsymmetrical aminals and consists of decomposing the starting N,O-acetal 1 by heating in vacuo in the presence of the desired arylamine. Ein einfacher und allgemeiner Zugang zu symmetrischen und unsymmetrischen Bis(arylamino)methanen. Rea…