Photooxygenation of Azidoalkyl Furans: Catalyst-Free Triazole and New Endoperoxide Rearrangement

KAZANCIOGLU, Elif Akin; KAZANCIOGLU, Mustafa Zahrittin; FISTIKCI, Meryem; Seçen, Hasan; Altundas, Ramazan

doi:10.1021/ol402163u

Makale Tam Makale Uluslararası 2013

Photooxygenation of Azidoalkyl Furans: Catalyst-Free Triazole and New Endoperoxide Rearrangement

Elif Akin KAZANCIOGLU, Mustafa Zahrittin KAZANCIOGLU, Meryem FISTIKCI, Hasan Seçen, Ramazan Altundas

ORGANIC LETTERS Cilt 15 · Sayı 18 · ss. 4790–4793 · 20.09.2013

DOI ile aç

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%.

Atıf için künye

KAZANCIOGLU, E. A., KAZANCIOGLU, M. Z., FISTIKCI, M., Seçen, H., & Altundas, R. (2013). Photooxygenation of Azidoalkyl Furans: Catalyst-Free Triazole and New Endoperoxide Rearrangement. ORGANIC LETTERS, 15(18), 4790–4793. https://doi.org/10.1021/ol402163u

BibTeX

@article{kazancioglu2013-71388,
  author = {KAZANCIOGLU, Elif Akin and KAZANCIOGLU, Mustafa Zahrittin and FISTIKCI, Meryem and Seçen, Hasan and Altundas, Ramazan},
  title = {Photooxygenation of Azidoalkyl Furans: Catalyst-Free Triazole and New Endoperoxide Rearrangement},
  journal = {ORGANIC LETTERS},
  year = {2013},
  volume = {15},
  number = {18},
  pages = {4790--4793},
  issn = {1523-7060},
  doi = {10.1021/ol402163u},
  url = {https://akademik.atauni.edu.tr/yayinlar/71388-photooxygenation-of-azidoalkyl-furans-catalyst-free-triazole-and-new}
}