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

  1. Barluenga, J. 1
  2. Bayón, A.M. 1
  3. Campos, P. 1
  4. Asensio, G. 2
  5. Gonzalez-Nuñez, E. 2
  6. Molina, Y. 2
  1. 1 Universidad de Oviedo
    info

    Universidad de Oviedo

    Oviedo, España

    ROR https://ror.org/006gksa02

  2. 2 Universitat de València
    info

    Universitat de València

    Valencia, España

    ROR https://ror.org/043nxc105

Journal:
Journal of the Chemical Society. Perkin Transactions 1 2001

ISSN: 1472-7781

Year of publication: 1988

Volume: 7

Pages: 1631-1636

Type: Article

DOI: 10.1039/P19880001631 SCOPUS: 2-s2.0-37049075613 WoS: WOS:A1988P354500001 GOOGLE SCHOLAR

More publications in: Journal of the Chemical Society. Perkin Transactions 1 2001

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Abstract

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.