Abstract
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 stereoc hemical results. The formation of a hydrogen bond along a particular reaction channel significan tly stabilizes both transition states and products related to cis -adducts. Biological tests indicate that the obtain ed compounds do not show relevant antiviral and anticancer activity.
Highlights
In these last years, the nucleoside structure has been exploited as an efficient template for the development of new therapeutically useful compounds.[1,2,3] In this context, structural modifications on the sugar moiety of natural nucleosides and/or modifications of the heterocyclic base have been performed
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
Summary
The nucleoside structure has been exploited as an efficient template for the development of new therapeutically useful compounds.[1,2,3] In this context, structural modifications on the sugar moiety of natural nucleosides and/or modifications of the heterocyclic base have been performed. The observed stereochemistry is in deep contrast with the precedent results reported for the cycloaddition reactions of this nitrone with various electron-rich, electron-poor and conjugative dipolarophiles, in which the trans adducts are the major stereoisomers.[8,30] to rationalize the observed high regio- and stereoselectivity, a computational study at DFT level[31,32,33,34] was performed using the M062X/6-31G(d,p) calculations.[35]
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