A concise synthesis of 2-amino-1,2,3,4-tetrahydronaphthalene-6,7-diol ('6,7-ADTN') from naphthalene-2,3-diol

Goksu S., Kazaz C., SUTBEYAZ Y., Secen H.

HELVETICA CHIMICA ACTA, cilt.86, sa.10, ss.3310-3313, 2003 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 86 Sayı: 10
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1002/hlca.200390272
  • Dergi Adı: HELVETICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3310-3313
  • Atatürk Üniversitesi Adresli: Evet

Özet

2-Amino-1,2,3,4-tetrahydronaphthalene-6,7-diol (2 6,7-ADTN) was synthesized starting from naphthalene-2.3-diol in seven steps and with an overall yield of 44%. Methylation of naphthalene-2.3-diol with dimethyl sulfate, followed by Friedel-Crafts acylation with AcCl, gave 2-acetyl-6,7-dimethoxynaphthalene. 2-Acetyl-6,7-dimethoxynaphthalene was converted to 6.7-dimethoxynaphthalene-2-carboxylic acid by a haloform reaction. Birch reduction of the carboxylic acid with 4 mol-equiv. of Na in liquid ammonia afforded 1,2,3,4-tetrahydro-6.7-dimethoxynaphthalene-2-carboxylic acid, from which 2 was obtained by a Curtius reaction, followed by hydrogenolysis and demethylation.