A comparison of N- versus O-alkylation of substituted 2-pyridones under Mitsunobu conditions

被引：27
|
作者：
Torhan, Matthew C. [1 ]
Peet, Norton P. [1 ]
Williams, John D. [1 ]
机构：
[1] Microbiotix Inc, Worcester, MA 01605 USA
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 30期
关键词：
2-Pyridone; Mitsunobu reaction; Ambident nucleophiles; N-alkylation; O-allcylation; DISCOVERY; AGENTS;
D O I：
10.1016/j.tetlet.2013.05.054
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Pyridones are well-known ambident nucleophiles which are capable of reacting with electrophiles through either the nitrogen or oxygen atom to form N-alkyl-2-pyridones or 2-alkoxypyridines, respectively. It has been shown that the ratio of these products can be affected by a number of factors including the nature of the electrophile, the base used for deprotonation, and the solvent. We have now discovered a relationship between the ratio of N- and O-alkylation products and the nature of substituents on the pyridone ring when the Mitsunobu reaction is used to alkylate 2-pyridones. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3926 / 3928
页数：3
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