Influence of Steric, Electronic, and Molecular Preorganization Effects in the Reactivity of β‐phenylethylamines with Nonenolizable Aldehydes

La tiramina y la N-benciltiramina reaccionan con formaldehído para formar azaciclofanos por medio de condensaciones tipo Mannich aromáticas y reaccionan con aldehídos no enolizables para formar las respectivas bases de Schiff. En este artículo se presenta la síntesis inesperada de N-bencil-N-formiltiramina y N-bencil-N-metiltiramina por medio de reacciones de transamidación y de transamidación-reducción de N-benciltiramina con N,N-dimetilformamida. Para explicar el curso de la reacción se propuso un mecanismo que involucra la formilación de N-benciltiramina y posterior reducción de Leuckart-Wallach inducida por ácido fórmico generado in situ.

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Influence of Steric, Electronic, and Molecular Preorganization Effects in the Reactivity of β‐phenylethylamines with Nonenolizable Aldehydes

Cited by 2 publications

References 43 publications

Synthesis and intermolecular interactions of N-benzylidenetyramines

Synthesis and intermolecular interactions of N-benzylidenetyramines

Transamidación y transamidación-reducción de N-benciltiramina con DMF

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