POLYSUBSTITUTED FUSED RING BICYCLIC THIOHYDANTOINS FROM AMINOCARBO-N-THIOYLPYRROLIDINES DERIVED FROM AZOMETHINE YLIDE 1,3-DIPOLAR CYCLOADDITIONS


Nural Y., DÖNDAŞ H. A. , Grigg R., ŞAHİN E.

HETEROCYCLES, vol.83, no.9, pp.2091-2114, 2011 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 83 Issue: 9
  • Publication Date: 2011
  • Doi Number: 10.3987/com-11-12276
  • Title of Journal : HETEROCYCLES
  • Page Numbers: pp.2091-2114

Abstract

Highly substituted bicyclic thiohydantoins fused to pyrrolidines were prepared from aminocarbo-N-thioylpyrrolidines derived from alpha-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.