Rearrangements of fused tetracyclic heterocycles induced by electrophiles

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Authors

ZACHOVÁ Hana MAN Stanislav TARABA Jan POTÁČEK Milan

Year of publication 2005
Type Article in Proceedings
Conference 11th Blue Danube Symposium on Heterocyclic Chemistry
MU Faculty or unit

Faculty of Science

Citation
Field Organic chemistry
Keywords rearrangement; criss-cross cycloaddition; allenyl
Description Intramolecular criss-cross cycloaddition reaction of symmetrical homoallenylazines is a specific type of successive 1,3-dipolar cycloaddition reactions. New fused tetracyclic compounds are formed in high yields by this reaction. In acidic conditions the criss-cross cycloadduct rearranges to completely new structure of heterocyclic compound with two six-membered and two five-membered rings. This new rearrangement was firstly monitored in the presence of reducing agent (NaBH3CN). A similar reaction is observed when an electrophile reagent instead of acid is used. When reducing agent is not used the stable quartery iminium salt is isolated.
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