Synthesis of new 4-aza-indoles via acyl azides

Dogan S. D., DEMİRPOLAT E., Aycan M. B. Y., BALCI M.

TETRAHEDRON, vol.71, no.2, pp.252-258, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 71 Issue: 2
  • Publication Date: 2015
  • Doi Number: 10.1016/j.tet.2014.11.057
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.252-258
  • Keywords: Acyl azide, Azaindole, Azaoxindole, Curtius rearrangement, Cytotoxic activity, SPONGE KIRKPATRICKIA-VARIALOSA, HOMOPHTHALIC ACID, REACTIVITY, AZAINDOLES, INDOLE, 5-AZAINDOLES, DERIVATIVES, INHIBITION, ALKALOIDS, ACCESS
  • Middle East Technical University Affiliated: Yes

Abstract

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.