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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

8 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

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo400364p

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

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.",

author = "Shih, {Yu Chiao} and Yang, {Ya Ying} and Lin, {Chun Chi} and Chien, {Tun Cheng}",

year = "2013",

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doi = "10.1021/jo400364p",

language = "English",

volume = "78",

pages = "4027--4036",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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T1 - Synthesis of 6-alkyluridines from 6-cyanouridine via zinc(II) chloride-catalyzed nucleophilic substitution with alkyl grignard reagents

AU - Shih, Yu Chiao

AU - Yang, Ya Ying

AU - Lin, Chun Chi

AU - Chien, Tun Cheng

PY - 2013/4/19

Y1 - 2013/4/19

N2 - 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.

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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U2 - 10.1021/jo400364p

DO - 10.1021/jo400364p

M3 - Article

C2 - 23535022

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

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

Abstract

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CCDC 948779: Experimental Crystal Structure Determination

CCDC 948780: Experimental Crystal Structure Determination

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 948779: Experimental Crystal Structure Determination

CCDC 948780: Experimental Crystal Structure Determination

Cite this