1,3-DIPOLAR CYCLOADDITION REACTIONS OF 3′,5′-<i>BIS</i>-<i>O</i>-SILYL THYMIDINES. SYNTHESIS OF NOVEL AZABICYCLIC COMPOUNDS

Negron, G.; Calderón, Gustavo; Vázquez, Francisco A. Rojo; Lomas, Leticia; Cárdenas, Jorge; Márquez, C.; Gaviño, Rubén

doi:10.1081/scc-120004847

Cited by 6 publications

(1 citation statement)

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“…Saladino et al [7] reported the reaction of lithium trimethylsilyldiazomethane and diazomethane with uracil. Pellissier et al [8] investigated the cobalt-mediated [2.2.2] cycloaddition of pyrimidine derivatives to alkynes, and Negron and coworkers obtained bicyclic N-methylpyrrolidine thymidine derivatives using cycloaddition reaction of azomethine ylide with bis-O-silylthymidines [9]. Finally, Colacino and coworkers obtained in reaction between nitrone and 1-N-vinyluracil a new isoxazolidine derivative fused with the pyrimidine moiety, as a competitive product to 4 0 -aza-analogues of 2 0 ,3 0 -dideoxynucleotides [10].…”

Section: Introductionmentioning

confidence: 99%

The nitrogen inversion in fused isoxazolidinyl derivatives of substituted uracil: synthesis, NMR and computational analysis

2016

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A series of fused isoxazolidines have been prepared via 1,3-dipolar cycloaddition reactions of N-protected methylenenitrones with 1,3-dimethyluracil derivatives, and their NMR spectra have been recorded in TFAd and in CDCl 3 over a wide range of temperatures. The spectra indicate the presence of two invertomers for all isoxazolidines. Barriers to nitrogen inversion in the cycloadduct 6a have been determined using DFT quantochemical calculations. Our estimates have shown that the inversion proceeds at more complex path, involving four structures of local minima and four transition states.

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