Article 2023 · 5 citations

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

Akincioglu, Akin, Akbaba, Yusuf, Kose, Leyla Polat, Akyuz, Leyla Demirkol, Goksu, Sueleyman

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.

Keywords

Dopaminergic compounds 2-Aminotetralin 2-Aminoindane Asymmetric resolution Mandelic acid O-acetylmandeloyl chloride ALPHA-ADRENERGIC AGENTS DOPAMINE AGONIST INHIBITORS CONGENERS ANALOGS SERIES ACID

WoS Categories

Chemistry, Organic

Sustainable Development Goals

Good Health and Well-being

Citation

Journal: TETRAHEDRON
Year: 2023
Volume: 133
ISSN: 0040-4020
eISSN: 1464-5416
DOI: 10.1016/j.tet.2023.133277
WoS UID: WOS:000944002300001

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