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, vol.133, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 133
  • Publication Date: 2023
  • Doi Number: 10.1016/j.tet.2023.133277
  • Journal Name: TETRAHEDRON
  • Journal Indexes: 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, Index Chemicus (IC)
  • Istanbul University Affiliated: No

Abstract

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.