A Novel Methodology for the Asymmetric Synthesis of 2,3,5-Trisubstituted Piperazine Derivatives

Beksultanova N., ÖZDEMİR YILDIRIM Ö., Çaklr S. P., AYGÜN M., DOĞAN Ö.

Synthesis (Germany), sa.15, ss.2432-2444, 2024 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1055/s-0040-1720114
  • Dergi Adı: Synthesis (Germany)
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex
  • Sayfa Sayıları: ss.2432-2444
  • Anahtar Kelimeler: asymmetric synthesis, aziridines, intramolecular cyclization, piperazines, Staudinger reaction
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

Piperazines constitute an important structural feature of many pharmaceuticals. For the discovery of new drugs, the ability to modify the lead compound s structure is crucial. Herein, we provide an efficient method for the synthesis of chiral 2,3,5-trisubstituted piperazine structures. Our route enables the synthesis of several novel chiral aryl aziridinyl ketones that could be converted into aziridine-fused bicyclic imines. The reduction of these imines and the nucleophilic ringopening reaction of the aziridine ring allowed us to synthesize highly functionalized piperazine derivatives.