Synthesis of fused tetrazolone derivatives

Özcan S., EKMEKÇİ Z., Müjde B., Balci M.

Turkish Journal of Chemistry, vol.37, no.4, pp.610-618, 2013 (SCI-Expanded, Scopus, TRDizin) identifier

  • Publication Type: Article / Article
  • Volume: 37 Issue: 4
  • Publication Date: 2013
  • Doi Number: 10.3906/kim-1303-90
  • Journal Name: Turkish Journal of Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.610-618
  • Keywords: 1,3-dipolar cycloaddition, 1,3-dipole, Acyl azide, Curtius rearrangement, Dipolarophile, Tetrazolone
  • Isparta University of Applied Sciences Affiliated: No

Abstract

New fused tetrazolone derivatives were synthesized using homophthalic and maleic anhydrides. Treatment of anhydrides with trimethylsilyl azide opened the lactone rings and formed the corresponding intermediates, which bore 1,3-dipole and dipolarophile functionalities in ortho positions. The intermediates partially underwent internal 1,3-dipolar cycloaddition to produce fused tetrazolone derivatives. When the carbonyl groups in anhydride were not conjugated with any double bond, then a triazine-fused tetrazolone derivative was formed. © TÜBITAK.