Synthesis of 6-alkyluridines from 6-cyanouridine via zinc(II) chloride-catalyzed nucleophilic substitution with alkyl grignard reagents

Yu Chiao Shih, Ya Ying Yang, Chun Chi Lin, Tun-Cheng Chien

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

6-Cyanouracil derivatives underwent a direct nucleophilic substitution reaction with alkyl Grignard reagents in the presence of zinc(II) chloride as a catalyst to form the corresponding 6-alkyluracils. This methodology is applicable to sugar-protected 6-cyanouridine and 6-cyano-2′-deoxyuridine without the protection at the N3-imide and provides a facile and general access to versatile 6-alkyluracil and 6-alkyluridine derivatives.

Original languageEnglish
Pages (from-to)4027-4036
Number of pages10
JournalJournal of Organic Chemistry
Volume78
Issue number8
DOIs
Publication statusPublished - 2013 Apr 19

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Imides
Zinc chloride
Deoxyuridine
Substitution reactions
Derivatives
Sugars
Catalysts
zinc chloride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of 6-alkyluridines from 6-cyanouridine via zinc(II) chloride-catalyzed nucleophilic substitution with alkyl grignard reagents. / Shih, Yu Chiao; Yang, Ya Ying; Lin, Chun Chi; Chien, Tun-Cheng.

In: Journal of Organic Chemistry, Vol. 78, No. 8, 19.04.2013, p. 4027-4036.

Research output: Contribution to journalArticle

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