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通过锌(II)氯化物催化的亲核取代反应,用烷基格氏试剂从 6-氰基尿苷合成 6-烷基尿嘧啶核苷。

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

机构信息

Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.

出版信息

J Org Chem. 2013 Apr 19;78(8):4027-36. doi: 10.1021/jo400364p. Epub 2013 Apr 9.

DOI:10.1021/jo400364p
PMID:23535022
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 N(3)-imide and provides a facile and general access to versatile 6-alkyluracil and 6-alkyluridine derivatives.

摘要

6-氰基尿嘧啶衍生物在氯化锌(II)作为催化剂的存在下与烷基格氏试剂发生直接亲核取代反应,形成相应的 6-烷基尿嘧啶。该方法适用于糖保护的 6-氰基尿苷和 6-氰基-2'-脱氧尿苷,而无需对 N(3)-酰亚胺进行保护,为多功能 6-烷基尿嘧啶和 6-烷基尿苷衍生物提供了一种简便通用的方法。

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