5-Triazolyl-2-methylisoxazolidin-3-yl 3-phosphonates have been synthesized by 1,3-dipolar cycloaddition of N-methyl-C-diethoxyphosphorylnitrone and vinyl triazoles. The process showed a complete regioselectivity and a nearly exclusive cis stereoselectivity. M062X/6-31G(d,p) calculations rationalize the regio- and the stereochemical results. The formation of a hydrogen bond along a particular reaction channel significantly stabilizes both transition states and products related to cis-adducts. Biological tests indicate that the obtained compounds do not show relevant antiviral and anticancer activity

5-(3-Phosphonated 1H-1,2,3-triazol-4-yl)isoxazolidines: synthesis, DFT studies and biological properties

GIOFRE', Salvatore Vincenzo;ROMEO, Roberto;CICERO, Nicola;
2015

Abstract

5-Triazolyl-2-methylisoxazolidin-3-yl 3-phosphonates have been synthesized by 1,3-dipolar cycloaddition of N-methyl-C-diethoxyphosphorylnitrone and vinyl triazoles. The process showed a complete regioselectivity and a nearly exclusive cis stereoselectivity. M062X/6-31G(d,p) calculations rationalize the regio- and the stereochemical results. The formation of a hydrogen bond along a particular reaction channel significantly stabilizes both transition states and products related to cis-adducts. Biological tests indicate that the obtained compounds do not show relevant antiviral and anticancer activity
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11570/3065390
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