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

doi:10.1021/jo400364p

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

Department of Chemistry

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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 language	English
Pages (from-to)	4027-4036
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	78
Issue number	8
DOIs	https://doi.org/10.1021/jo400364p
Publication status	Published - 2013 Apr 19

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ASJC Scopus subject areas

Organic Chemistry

Cite this

Shih, Y. C., Yang, Y. Y., Lin, C. C., & Chien, T-C. (2013). Synthesis of 6-alkyluridines from 6-cyanouridine via zinc(II) chloride-catalyzed nucleophilic substitution with alkyl grignard reagents. Journal of Organic Chemistry, 78(8), 4027-4036. https://doi.org/10.1021/jo400364p

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AU - Chien, Tun-Cheng

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AB - 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.

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10.1021/jo400364p