Synthesis of highly functionalized 2-(pyrrolidin-1-yl)thiazole frameworks with interesting antibacterial and antimycobacterial activity

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Belveren S., DÖNDAŞ H. A., Ulger M., Poyraz S., Garcia-Minguens E., Ferrandiz-Saperas M., ...Daha Fazla

TETRAHEDRON, cilt.73, sa.48, ss.6718-6727, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 73 Sayı: 48
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.tet.2017.10.007
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.6718-6727
  • Anahtar Kelimeler: Antimycobacterial, Antibacterial, Thiazole, Prolinates, PICTET-SPENGLER REACTIONS, 1,3-DIPOLAR CYCLOADDITION, AZOMETHINE YLIDES, POTENTIAL 1,3-DIPOLES, INHIBITORS, SYSTEMS, HETEROCYCLES, PYRROLIDINE, COMBINATION, DERIVATIVES
  • Çukurova Üniversitesi Adresli: Hayır

Özet

A versatile, facile and concise approach to access to highly substituted functionalized 2-(pyrrolidin-1-yl)thiazole ring system is accomplished. The efficient protocol proceeds by the reaction of corresponding racemic or enantiomerically enriched pyrrolidines and readily available benzoylisothiocyanate in acetonitrile followed by sequential reaction of readily available alpha-bromo ketones in acetone. The selectivity and good yield in the desired product is another important advantage of this reaction protocol. In a few cases, the resulting N-benzoylthiourea intermediate cyclizes spontaneously before reacting with the benzophenone component. Finally, a wide study of the biological scope of this new bisheterocyclic molecules is reported. (C) 2017 Elsevier Ltd. All rights reserved.