Alternative and Straightforward Synthesis of Dopaminergic 5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine

OZTASKIN N., GÖKSU S., SEÇEN H.

SYNTHETIC COMMUNICATIONS, cilt.41, sa.13, ss.2017-2024, 2011 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 41 Sayı: 13
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1080/00397911.2010.495043
  • Dergi Adı: SYNTHETIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2017-2024
  • Anahtar Kelimeler: Aminotetralin, Birch reduction, Curtius rearrangement, dopamine, neurotransmitter, synthesis
  • Atatürk Üniversitesi Adresli: Evet

Özet

[image omitted] 5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine was synthesized from 2-naphthoic acid in six steps with an overall yield of 27%. Following the reaction sequence, bromination, esterification, substitution with NaOMe in the presence of CuI, the Birch reduction, Curtius rearrangement, and hydrogenolysis afforded biologically active title compound 5-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine as hydrogen chloride salt.