Photooxygenation of azidoalkyl furans: Catalyst-free triazole and new endoperoxide rearrangement


Kazancioglu E. A., Kazancioglu M. Z., Fistikci M., SEÇEN H., Altundas R.

Organic Letters, vol.15, no.18, pp.4790-4793, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 15 Issue: 18
  • Publication Date: 2013
  • Doi Number: 10.1021/ol402163u
  • Journal Name: Organic Letters
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4790-4793
  • Hakkari University Affiliated: No

Abstract

Photooxygenation of azidoalkyl furans has revealed both a novel triazole formation method and a unique endoperoxide rearrangement. The key step of this method is a 3 + 2 cycloaddion of the azide to the endoperoxide intermediate. The reduction of the peroxide bond and two subsequent C-C bond cleavages provide a triazole having a newly formed carboxylic acid functionality. The reactions are clean and efficient with yields ranging from 60% to 90%. © 2013 American Chemical Society.