Oxidation of aminoalkyl and hydroxylaminoalkyl furans

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

doi:10.1016/j.tetlet.2015.10.105

Makale Tam Makale Uluslararası 2015

Oxidation of aminoalkyl and hydroxylaminoalkyl furans

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

Tetrahedron Letters Cilt 56 · Sayı 50 · ss. 6994–6997 · 16.12.2015

DOI ile aç

Özet

The oxidation reactions of amino and hydroxylamino substituted alkylfurans were explored for the synthesis of structurally complex compounds from simple starting materials. A novel photooxygenation of the furan derivatives gave an alpha,beta-unsaturated dicarbonyl moiety which underwent subsequent conjugate addition to yield diastereomeric mixtures of the corresponding pyrrolidine and isoxazoline heterocycles. Oxidation of the alpha,beta-unsaturated dicarbonyl using mCPBA gave epoxide intermediates, which were opened by nucleophilic attack of the amino groups, furnishing pyrrolidine and isoxazolidine heterocycles. (C) 2015 Elsevier Ltd. All rights reserved.

Anahtar kelimeler

oxidation Aminoalkylfuran Hydroxylaminofuran Substituted pyrrolidine Substituted isooxazoline

Atıf için künye

KAZANCIOGLU, M. Z., KAZANCIOGLU, E. A., Seçen, H., & Altundas, R. (2015). Oxidation of aminoalkyl and hydroxylaminoalkyl furans. Tetrahedron Letters, 56(50), 6994–6997. https://doi.org/10.1016/j.tetlet.2015.10.105

BibTeX

@article{kazancioglu2015-71426,
  author = {KAZANCIOGLU, Mustafa Zahrittin and KAZANCIOGLU, Elif Akin and Seçen, Hasan and Altundas, Ramazan},
  title = {Oxidation of aminoalkyl and hydroxylaminoalkyl furans},
  journal = {Tetrahedron Letters},
  year = {2015},
  volume = {56},
  number = {50},
  pages = {6994--6997},
  issn = {0040-4039},
  doi = {10.1016/j.tetlet.2015.10.105},
  url = {https://akademik.atauni.edu.tr/yayinlar/71426-oxidation-of-aminoalkyl-and-hydroxylaminoalkyl-furans}
}