Rearrangements of fused tetracyclic heterocycles induced by electrophiles
| Authors | |
|---|---|
| Year of publication | 2005 |
| Type | Article in Proceedings |
| Conference | 11th Blue Danube Symposium on Heterocyclic Chemistry |
| MU Faculty or unit | |
| 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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