Sur le mécanisme des synthéses de l'isoquinoléine à partir de dérivés de la benzylamine

Acid-catalyzed cyclization of benzalaminoacetal results in the formation of the isoquinoline nucleus. This reaction, first reported by Pomeranz and Fritsch, has been used in the synthesis of a variety of isoquinoline compounds. The process is carried out in two stages. In step one, a condensation leads to the benzalaminacetal. In step two, a ring closure leads to the isoquinoline. An alternative route involves the condensation of the corresponding benzylamine witth glyoxal semiacetal. The yield of isoquinoline products varies widely. The Pomeranz-Fritsch synthesis offers the possibility of preparing isoquinolines with the substituent groups in an orientation difficult to achieve with other methods.


Keywords:

Pomeranz-Fritsch reaction;
isoquinolines;
cyclization;
Schiff base;
acetals;
glyoxyl semiacetal;
experimental procedures

The Synthesis of Isoquinolines by the Pomeranz‐Fritsch Reaction

Untersuchungen in der Reihe der Isochinoline. IV. Teil. Synthesen von Benzo‐Isochinolonen und Untersuchung der Methoden, Isochinoline aus dem Naphthalinring herzustellen

Untersuchungen in der Reihe der Isochinoline. I. Teil. Versuche zur Synthese von Isochinolinderivaten aus substituierten Benzylaminen

Über tertiäre Aminoketone und ihre Anwendung zu Ringsynthesen

/pdf/ueber-einige-derivate-des-benzylamins-257ocllbcf.pdf

R. Kuphal

Papers

Ueber einige Derivate des Benzylamins