Synthesis and asymmetric resolution of substituted 2-aminoindane and 2-aminotetralin derivatives

Akincioglu A., AKBABA Y., Kose L. P., Akyuz L. D., Goksu S.

TETRAHEDRON, cilt.133, 2023 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 133
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1016/j.tet.2023.133277
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aquatic Science & Fisheries Abstracts (ASFA), BIOSIS, Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Chimica, EMBASE, Veterinary Science Database
  • Anahtar Kelimeler: Dopaminergic compounds, 2-Aminotetralin, 2-Aminoindane, Asymmetric resolution, Mandelic acid, O-acetylmandeloyl chloride, ALPHA-ADRENERGIC AGENTS, DOPAMINE, AGONIST, INHIBITORS, CONGENERS, ANALOGS, SERIES, ACID
  • İstanbul Üniversitesi-Cerrahpaşa Adresli: Hayır

Özet

We performed the racemic synthesis and asymmetric resolution of one 2-aminoindane and three 2-aminotertalins due to their crucial biological roles in the central nervous system (CNS). For this reason, desired (+/-)-2-aminoindane and (+/-)-2-aminotetralin derivatives were synthesized starting from appropriate reagents. While highly enantio pure (+)-39, (+)-40, and ( inverted exclamation )-40 were obtained from the reaction of racemic amines with (R)-O-acetylmandeloyl chloride followed by crystallization, hydrolysis with KOH and acidification with HCl, (S)-42 and (-)-43 were synthesized via the reaction of racemic amines with (S)-mandelic acid and hydrolysis.(c) 2023 Elsevier Ltd. All rights reserved.