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Paper | Regular issue | Vol 83, No. 9, 2011, pp.2091-2114
Published online, 22nd July, 2011
DOI: 10.3987/COM-11-12276
Polysubstituted Fused Ring Bicyclic Thiohydantoins from Aminocarbo-N-thioylpyrrolidines Derived from Azomethine Ylide 1,3-Dipolar Cycloadditions

Yahya Nural, H. Ali Döndaş,* Ronald Grigg, and Ertan Şahin

*Department of Chemistry, Faculty of Pharmacy, Mersin University, 33342, Mersin, Turkey

Abstract

Highly substituted bicyclic thiohydantoins fused to pyrrolidines were prepared from aminocarbo-N-thioylpyrrolidines derived from α-amino acid esters via imine azomethine ylide 1,3-dipolar cycloadditions and subsequent reaction with aroylisothiocyanates. Aminocarbo-N-thioylpyrrolidines efficiently undergo cyclisation in the presence of sodium methoxide to form bicyclic N-substituted thiohydantoins with concomitant cleavage of the N-acyl group in good to excellent yield. And also some interesting both regiospecific and stereospecific rearrangement to the bicyclic fused thiocarbamoil pyrrolidine and bicyclic thiohydantoin were observed.