Bruckner isoquinoline synthesis

What is Bruckner isoquinoline synthesis?

The Bruckner isoquinoline synthesis can be traced back to 1935 when Bruckner determined the structure of 1,3-dimethyl-6,7-methylenedioxyisoquinoline.

Bruckner isoquinoline synthesis
Bruckner isoquinoline synthesis

This reaction is a distinctive approach to creating isoquinolines from allyl phenyl ether, involving a Claisen rearrangement, double-bond migration, amination, and cyclization.

References

Bruckner, V. (1935), Über die Verwendung der Pseudo-nitrosite propenyl-haltiger Phenol-äther zur Synthese von α-arylierten β-Hydroxylamino-und β-Amino-propanolen. Neue Beiträge zur Kenntnis der Acylwanderungen. Methyl-isoeugenol- und Isosafrol-Derivate. [On the use of the pseudo-nitrosite of propenyl-containing phenolic ethers for the synthesis of α-arylated β-hydroxylamino and β-amino-propanols. New contributions to the knowledge of acyl migrations. Methyl isoeugenol and isosafrole derivatives.] Justus Liebigs Ann. Chem., 518: 226-244. https://doi.org/10.1002/jlac.19355180114

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