Synthesis of new 4-aza-indoles via acyl azides

Dogan S. D., DEMİRPOLAT E., AYCAN M. B., BALCI M.

TETRAHEDRON, cilt.71, sa.2, ss.252-258, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 71 Sayı: 2
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.tet.2014.11.057
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.252-258
  • Anahtar Kelimeler: Acyl azide, Azaindole, Azaoxindole, Curtius rearrangement, Cytotoxic activity, SPONGE KIRKPATRICKIA-VARIALOSA, HOMOPHTHALIC ACID, REACTIVITY, AZAINDOLES, INDOLE, 5-AZAINDOLES, DERIVATIVES, INHIBITION, ALKALOIDS, ACCESS
  • Erciyes Üniversitesi Adresli: Evet

Özet

We hereby report the preparation of new azaindole derivatives starting from 2-(2-ethoxy-2-oxoethyl) nicotinic acid. Conversion of a half ester into acyl azide followed by Curtius rearrangement gave the corresponding isocyanate. Trapping of the isocyanate with different nucleophiles produced urea and urethane derivatives. Intramolecular cyclization reactions gave the target compounds. (C) 2014 Elsevier Ltd. All rights reserved.