Halogenation of 5-substituted-6,2'-O-cyclouridines afforded 6,2':6,5'-dianhydro-5,6-dihydro-6, 6-dihydroxy-5-halo-5-substituted-uracil arabinosides. Their steric configurations and mass spectra were also discussed.
Reaction of 5-chloro (or bromo)-6, 2'-O-cyclouridine (IIa or IIb) with N-bromo(or chloro)-succinimide gave 5-bromo-5-chloro-5, 6-dihydro-6, 2' : 6, 5'-di-O-cyclouridine (VI). A similar reaction of 5-nitro-6, 2'-O-cyclouridine (VII) afforded the 5-chloro(or bromo)-5-nitro analog (VIII or IX). Both VI and VIII were mixtures of two diastereoisomers and each isomeric mixture was separated by preparative high-performance liquid chromatography. The steric configurations and mass spectra of VI, VIII and IX are discussed.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTHalogenation of pyrimidine 6-O-cyclonucleosidesTokumi Maruyama, Shuhei Kimura, Yoshiko Sato, and Mikio HonjoCite this: J. Org. Chem. 1983, 48, 16, 2719–2723Publication Date (Print):August 1, 1983Publication History Published online1 May 2002Published inissue 1 August 1983https://pubs.acs.org/doi/10.1021/jo00164a016https://doi.org/10.1021/jo00164a016research-articleACS PublicationsRequest reuse permissionsArticle Views200Altmetric-Citations14LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts
Abstract 6,2′‐O‐Cyclouridin (I) ergibt mit Halogenen oder mit N‐Halogensuccinimiden die Halogenverbindungen (II) und bei weiterer Reaktion die Bis‐Cyclo‐Derivate (III), die auch aus (IV) erhalten werden können.
Abstract Reaction of 5‐bromo‐2,4‐dimethoxypyrimidine (I) with butyllithium and diethyl chlorophosphite (II) produces the phosphinate (III) which is hydrolyzed to yield uracil‐5‐phosphinic acid (IV).
