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...

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Detalles Bibliográficos
Autores: Barluenga, J. [0000-0002-6474-7782], Bayón, A.M., Campos, P. [0000-0002-8917-0318], Asensio, G. [0000-0001-5060-4417], Gonzalez-Nuñez, E. [0000-0003-4170-4568], Molina, Y.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:1988
País:España
Institución:Universidad de La Rioja (UR)
Repositorio:RIUR. Repositorio Institucional de la Universidad de La Rioja
OAI Identifier:oai:portal.dialnet.es:doc/5bbc68b9b750603269e80e50
Acceso en línea:https://investigacion.unirioja.es/documentos/5bbc68b9b750603269e80e50
Access Level:acceso abierto
Descripción
Sumario: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.

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