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Synthesis of Fused Tricyclic Hydantoins of Homotriquinane Type
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1  Institute for Information Technologies Kragujevac, Department of Science, University of Kragujevac, Jovana Cvijica bb, 34000 Kragujevac, Serbia

Abstract: Synthesis of tricyclic hydantoins with angularly fused rings was performed in three-step reaction sequence. Spiro-bicyclic hydantoins with alkenyl moiety, prepared from 2-alkenylcyclohexanones using Bucherer-Bergs reaction, were subjected to amidoselenylation reaction. This selenium-induced intramolecular cyclization is a key step of this sequence. The cyclization is regiospecific and formation of sole regioisomer proceeds via favorable 5-exo-trig ring closure process giving only homotriquinane type tricyclic hydantoins.
Keywords: Hydantoins; intramolecular cyclization; selenium; fused rings