O-tetrahydropyran-2-yloxy (O-THP) as an ortho-directing group in the lithiation of pyridines

被引：15

作者：

Azzouz, Rabah ^{[1
]}

Bischoff, Laurent ^{[1
]}

Fruit, Corinne ^{[1
]}

Marsais, Francis ^{[1
]}

机构：

[1] INSA, CNRS, UMR 6014, IRCOF,Lab Chim Organ Fine & Heterocycl, F-76131 Mont St Aignan, France

来源：

SYNLETT | 2006年 / 12期

关键词：

acetals; pyridines; metallations; lithium; organometallic reagents;

D O I：

10.1055/s-2006-947340

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report regioselective deprotonations of 3- and 4-(tetrahydropyran-2-yloxy)pyridine with n-butyllithium. Trapping the lithiated species with various electrophiles afforded functionalized pyridines in good yields. A one-pot procedure also allowed the double functionalization at C4 and C2 in the case of 3-O-THP-pyridine. The ortho-metallating ability of this group was examined in comparison with other well-known oxygen-based ortho-directing groups.

引用

页码：1908 / 1912

页数：5

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