Concise syntheses of 2-aminoindans via indan-2-ol

Goksu S., Secen H.

TETRAHEDRON, cilt.61, sa.28, ss.6801-6807, 2005 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 61 Sayı: 28
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1016/j.tet.2005.04.069
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.6801-6807
  • Anahtar Kelimeler: 2-aminoindans, synthesis, 2-azidoindans, 2-indanols, Mitsunobu reactions, dopamine, DOPAMINE D-3 RECEPTOR, ANTAGONIST PNU-99194A, PNU 99194A, ACID GABOB, (+)-7-OH-DPAT, SUBSTITUTION, SYSTEM, AZIDES, ESTER, RATS
  • Atatürk Üniversitesi Adresli: Evet

Özet

2-Amino-5,6-dimethoxyindan hydrochloride was synthesized in seven steps and with an overall yield of 48%. Indan-2-ol was converted to 5,6-dibromo-indan-2-ol in three steps by acetylation, electrophilic bromination and deacetylation. Dimethoxylation of 5,6-dibromoindan-2-ol with NaOCH3 in the presence of CuI gave 5,6-dimethoxy-indan-2-ol, which was converted to 2-amino-5,6-dimethoxyindan hydrochloride by azidation, followed by Pd-C catalyzed hydrogenation. Similarly, 2-amino-5-bromoindan was synthesized in five steps and with an overall yield of 50%. Indan-2-ol was converted to 2-aminoindan by azidation followed by Pd-C catalyzed hydrogenation. The reaction of 2-aminoindan with 2.5 equiv Br-2 afforded 2-amino-5,6-dibromoindan. (c) 2005 Elsevier Ltd. All rights reserved.