Synthesis of Fused Tricyclic Hydantoins of Homotriquinane Type

Biljana Smit; Radoslav Pavlovic

doi:10.3390/ecsoc-18-a021

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Ebselen-like Catalysts – New Approach

Synthesis of Fused Tricyclic Hydantoins of Homotriquinane Type

Biljana M Smit

^*,

Radoslav Z Pavlovic

¹ Institute for Information Technologies Kragujevac, Department of Science, University of Kragujevac, Jovana Cvijica bb, 34000 Kragujevac, Serbia

Published: 31 October 2014 by MDPI in The 18th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-18-a021

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

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Biljana Smit

Radoslav Pavlovic