An alternative synthesis of the dopaminergic drug 2-amino-1,2,3,4-tetrahydronaphthalene-5,6-diol (5,6-ADTN)

Goksu S., Secen H., Sütbeyaz Y.

HELVETICA CHIMICA ACTA, cilt.89, sa.2, ss.270-273, 2006 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 89 Sayı: 2
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1002/hlca.200690030
  • Dergi Adı: HELVETICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.270-273
  • Atatürk Üniversitesi Adresli: Evet

Özet

Racemic 2-amino-1,2,3,4-tetrahydronaphthalene-5,6-diol (5,6-ADTN; 4) was synthesized from 5,6-dimethoxynaphthalene-2-carboxylic acid (14) in four steps (60% overall yield; Scheme). The crucial steps of the synthesis are Birch reduction of 14 to the valuable synthon 15, Curtius reaction and carbamate formation (16), hydrogenolysis (17), and demethylation to the biologically active hydrobromide salt 18 of 4.