Abstract

DIAZ-OVIEDO, Christian  and  QUEVEDO, Rodolfo. Transamidation and transamidation-reduction of N-benzyltyramine with DMF. Rev.Colomb.Quim. [online]. 2018, vol.47, n.1, pp.5-9. ISSN 0120-2804.  https://doi.org/10.15446/rev.colomb.quim.v47n1.63976.

Tyramine and N-benzyltyramine react with formaldehyde to form azacyclophanes by means of aromatic Mannich reactions and react with non-enolizable aldehydes to form the respective Schiff bases. In this paper we present the unexpected synthesis of N-formyl-N-benzyltyramine and N-methyl-N-benzyltyramine by means of transamidation and transamidation-reduction of N-benzyltyramine with N,N-dimethylformamide. A reaction mechanism involving formylation of N-benzyltiramine followed by a Leuckart-Wallach reduction is proposed for rationalising such transformation.

Keywords : carboxamide; dimethylformamide; Leuckart-Wallach; tyramine.

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