1,3-Dipolar cycloaddition reactions of acyl phosphonates with nitrile oxides: synthesis of phosphonate-containing dioxazole derivatives

Polat Çakır S.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, cilt.196, sa.5, ss.461-467, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 196 Sayı: 5
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1080/10426507.2020.1854259
  • Dergi Adı: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Sayfa Sayıları: ss.461-467
  • Anahtar Kelimeler: 1,3-Dipolar cycloaddition, acyl phosphonate, dioxazole, dipole and dipolarophile, heterocyclic
  • Çanakkale Onsekiz Mart Üniversitesi Adresli: Evet

Özet

New phosphonate-containing five-membered heterocyclic dioxazole derivatives are synthesized via 1,3-dipolar cycloaddition reactions of nitrile oxides used as dipole with acyl phosphonates under basic conditions. Herein, acyl phosphonates take part in the cyclization process as a dipolarophile to afford the related dioxazole compounds in moderate-to-good yields (49-84%). Substituted aryl nitrile oxides and aroyl phosphonates were employed in the 1,3-dipolar cycloaddition reactions where triethylamine was the effective tertiary base. Alkyl version of acyl phosphonate also afforded the expected cycloadduct, that is, dimethyl 5-isopropyl-3-phenyl-1,4,2-dioxazol-5-yl-5-phosphonate. Diethyl/dimethyl 3,5-aryl-1,4,2-dioxazol-5-yl-5-phosphonate derivatives are fully characterized by using H-1 NMR, C-13 NMR, P-31-NMR, and FT along with high-resolution mass spectroscopy.