doi: 10.1021/jo0345648.
5-Endo-dig electrophilic cyclization of alpha-alkynyl carbonyl compounds: synthesis of novel bicyclic 5-iodo- and 5-bromofuranopyrimidine nucleosides
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- PMID: 12919049
- DOI: 10.1021/jo0345648
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5-Endo-dig electrophilic cyclization of alpha-alkynyl carbonyl compounds: synthesis of novel bicyclic 5-iodo- and 5-bromofuranopyrimidine nucleosides
J Org Chem.
.
Abstract
5-Endo-dig electrophilic cyclization of 5-alkynyl-2'-deoxyuridines with N-iodosuccinimide or N-bromosuccinimide in acetone at room temperature gives 3-(2'-deoxy-beta-D-ribofuranosyl)-5-halo-2,3-dihydrofuro[2,3-d]pyrimidin-2-ones that usually precipitate from the reaction mixture (86-74%).
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