A New Access to 1-Naphthylamines by an Equivalent Semmler-Wolff Reaction

Yves L. Janin; Emile Bisagni

doi:10.1055/s-1993-25792

Synthesis 1993; 1993(1): 57-59
DOI: 10.1055/s-1993-25792

short paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A New Access to 1-Naphthylamines by an Equivalent Semmler-Wolff Reaction

Yves L. Janin^* , Emile Bisagni

^*URA 1387 CNRS Institut Curie, Section de Biologie, Bat. 110 Centre Universitaire, F-91405 Orsay, France

Abstract

PDF Download All articles of this category

A new access to 1-naphthylamines from the corresponding 3,4-di-hydro-1(2H)-naphthalenones (α-tetralones) is described. It proceeds in a two-step sequence: preparation of the benzyl Schiff's base of an α-tetralone followed by aromatization over palladium catalyst, which happened to hydrogenolyze the benzyl group at the same time. Five 1-naphthylamines were prepared using this alternative path to the Semmler-Wolff reaction.

PDF (247 kb)