SIDE-CHAIN LITHIATION OF 2-AND 4-SUBSTITUTED PYRIDINES: SYNTHESIS OF MORE COMPLEX SUBSTITUTED PYRIDINES

被引：11

作者：

Smith, Keith ^{[1
]}

El-Hiti, Gamal A. ^{[1
]}

Fekri, Ahmed ^{[1
]}

Alshammari, Mohammed B. ^{[1
]}

机构：

[1] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, S Glam, Wales

来源：

HETEROCYCLES | 2012年 / 86卷 / 01期

关键词：

Organolithium; Side-Chain Lithiation; Heterocycle; Substituted Pyridine; Synthesis; DIRECTED ORTHO-METALATION; ELECTROPHILIC SUBSTITUTION; REGIOSELECTIVE LITHIATION; STEREOSELECTIVE LITHIATION; ORGANOLITHIUM REAGENTS; DIAZINES PYRIDINES; DERIVATIVES; CARBONYLATION; ACCESS; AMINES;

D O I：

10.3987/COM-12-S(N)33

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithiation of pyridines substituted in the 2- and 4-positions by acylaminomethyl groups, namely of the corresponding N-(pyridinylmethyl)pivalamides, N'-(pyridinylmethyl)-N,N-dimethylureas and tert-butyl N-pyridinylmethylcarbamates, with two mole equivalents of t-BuLi in anhydrous THF at -78 degrees C takes place on the nitrogen and on the methylene group of the side-chain. The lithium reagents thus obtained react with a variety of electrophiles to give the corresponding side-chain substituted derivatives in high yields.

引用

页码：391 / 410

页数：20

共 50 条

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