1, 3-Dipolar cycloaddition reactions of acyl phosphonates with nitrile oxides: synthesis of phosphonate-containing dioxazole derivatives. (28th November 2020)

• Record Type: Journal Article
• Authors: Polat-Cakir, Sidika
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 196:Number 5(2021)
• Page Start: 461
• Page End: 467
• Publication Date: 2020-11-28
• Subjects: 1, 3-Dipolar cycloaddition -- acyl phosphonate -- dioxazole -- heterocyclic -- dipole and dipolarophile; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2020.1854259
• Languages: English
• ISSNs: 1042-6507

Abstract

Abstract: 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 1 H NMR, 13 C NMR, 31 P-NMR, and FT along with high-resolution mass spectroscopy. Graphical Abstract: