Preparation of N-(alk-1-enyl) nucleobase compounds by Horner and Horner-Wadsworth-Emmons reactions

被引：10

作者：

Boesen, T ^{[1
]}

Madsen, C ^{[1
]}

Henriksen, U ^{[1
]}

Dahl, O ^{[1
]}

机构：

[1] Univ Copenhagen, HC Orsted Inst, Dept Chem, DK-2100 Copenhagen, Denmark

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 13期

关键词：

D O I：

10.1039/b002744h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of new N-9-(alk-1-enyl)adenines and N-1-(alk-1-enyl)thymines has been prepared by Horner reactions of the new phosphine oxides N-9-(diphenylphosphorylmethyl)adenine and N-1-(diphenylphosphorylmethyl)thymine derivatives 13a-c, or Horner-Wadsworth-Emmons reactions of the corresponding new phosphonates 14a-b, with benzaldehyde and various ketones. Yields were highest for the Horner reactions (10-79%), and were limited by steric hindrance, enolization of the ketones, and decomposition of some of the N-1-(alk-1-enyl)thymines in the presence of excess base (NaH). Butanal gave mixtures of products under Horner conditions, probably because aldol reactions intervened.

引用

页码：2015 / 2021

页数：7

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