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, cilt.83, sa.9, ss.2091-2114, 2011 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 83 Sayı: 9
  • Basım Tarihi: 2011
  • Doi Numarası: 10.3987/com-11-12276
  • Dergi Adı: HETEROCYCLES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2091-2114
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.