A Short and Convenient Synthesis of New 1,2-Disubstituted Carbocyclic Nucleoside Analogues of Pyrimidine Based on a Cyclopentene Ring

Abstract

The synthesis of a new series of 1,2-disubstituted carbonucleoside analogues, pyrimidines of general structure I, is reported. These compounds were prepared in good yield from (±)-6-azabicyclo[3.2.0]hept-3-en-7-one (1) via two synthetic routes that involve NaBH₄-mediated C-N bond cleavage as the key step. The uracil derivative Ia was halogenated with Cl, Br, and I at position 5 by treatment with the corresponding N-halosuccinimide.

Key words

nucleosides - reductions - amino alcohols - carbocycles - heterocycles

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