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

Akıncıoğlu, Akın; Akbaba, Yusuf; Köse, Leyla Polat; Akyüz, Leyla Demirkol; Göksu, Süleyman

doi:10.1016/j.tet.2023.133277

Makale Tam Makale Uluslararası 2023

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

Akın Akıncıoğlu, Yusuf Akbaba, Leyla Polat Köse, Leyla Demirkol Akyüz, Süleyman Göksu

TETRAHEDRON Cilt 133 · 03.03.2023

DOI ile aç

Özet

© 2023 Elsevier LtdWe 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 (−)-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.

Anahtar kelimeler

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

Atıf için künye

Akıncıoğlu, A., Akbaba, Y., Köse, L. P., Akyüz, L. D., & Göksu, S. (2023). Synthesis and asymmetric resolution of substituted 2-aminoindane and 2-aminotetralin derivatives. TETRAHEDRON, 133. https://doi.org/10.1016/j.tet.2023.133277

BibTeX

@article{akincioglu2023-72152,
  author = {Akıncıoğlu, Akın and Akbaba, Yusuf and Köse, Leyla Polat and Akyüz, Leyla Demirkol and Göksu, Süleyman},
  title = {Synthesis and asymmetric resolution of substituted 2-aminoindane and 2-aminotetralin derivatives},
  journal = {TETRAHEDRON},
  year = {2023},
  volume = {133},
  issn = {0040-4020},
  doi = {10.1016/j.tet.2023.133277},
  url = {https://akademik.atauni.edu.tr/yayinlar/72152-synthesis-and-asymmetric-resolution-of-substituted-2-aminoindane-and-2}
}