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Cycloadditions of isoquinolinium N-arylimides to enamines

✍ Scribed by Rolf Huisgen; Tony Durst; Robert Temme

Book ID
102892856
Publisher
Journal of Heterocyclic Chemistry
Year
1998
Tongue
English
Weight
511 KB
Volume
35
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The azomethine imine group of isoquinolinium N‐arylimides 2 is partially incorporated into an aromatic ring. The nucleophilic‐electrophilic 1,3‐dipoles 2 undergo cycloadditions to ethylene derivatives bearing either electron‐withdrawing or electron‐releasing substituents. The regiochemistry is bidirectional; electron‐attracting substituents appear at the 1‐position of the tricyclic adducts. Various enamines, however, adopt an orientation such that the amino function appears at the 2‐position. The tricyclic adducts undergo an acid‐catalyzed hyrazo rearrangement.

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