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, cilt.15, sa.18, ss.4790-4793, 2013 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 15 Sayı: 18
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1021/ol402163u
  • Dergi Adı: Organic Letters
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.4790-4793
  • Hakkari Üniversitesi Adresli: Hayır

Özet

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.