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Cycloadditions of isoquinolinium N ‐arylimides to enamines
Author(s) -
Huisgen Rolf,
Durst Tony,
Temme Robert
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350323
Subject(s) - chemistry , electrophile , tricyclic , regioselectivity , imine , nucleophile , adduct , ring (chemistry) , medicinal chemistry , enamine , stereochemistry , nucleophilic addition , polar effect , catalysis , organic chemistry
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.