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 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
  • Atatürk Üniversitesi Adresli: Evet

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%.