EventsThe 18th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-18-a021
This submission belongs to the session a. General Organic Synthesis of the event The 18th International Electronic Conference on Synthetic Organic Chemistry
Published date
31 Oct, 2014
Citation
Biljana M Smit, Radoslav Z Pavlovic, Synthesis of Fused Tricyclic Hydantoins of Homotriquinane Type, in Proceedings of The 18th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2014, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-18-a021
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Synthesis of Fused Tricyclic Hydantoins of Homotriquinane Type

Biljana M Smit 1
Radoslav Z Pavlovic 1
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
Manuscript
Biljana Smit ECSOC 18.pdf
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