Regioselective and Transition-Metal-Free Addition of tert-Butyl Magnesium Reagents to Pyridine Derivatives: A Convenient Method for the Synthesis of 3-Substituted 4-tert-Butylpyridine Derivatives

被引：11
|
作者：
Rappenglueck, Sebastian [1 ]
Niessen, Karin V. [2 ]
Seeger, Thomas [2 ]
Worek, Franz [2 ]
Thiermann, Horst [2 ]
Wanner, Klaus T. [1 ]
机构：
[1] Ludwig Maximilians Univ Munchen, Dept Pharm, Zentrum Pharmaforsch, Butenandtstr 5-13,Haus C, D-81377 Munich, Germany
[2] Bundeswehr Inst Pharmacol & Toxicol, Neuherbergstr 11, D-80937 Munich, Germany
来源：
SYNTHESIS-STUTTGART | 2017年 / 49卷 / 17期
关键词：
3,4-disubstituted pyridines; N-activation; heterocycles; diorganomagnesium; nucleophilic addition; microwave; CROSS-COUPLING REACTIONS; GRIGNARD-REAGENTS; FACILE SYNTHESIS; ALKYLATION; SALTS; HETEROCYCLES; ANTAGONISTS; NICOTINE; ESTERS; COPPER;
D O I：
10.1055/s-0036-1589025
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A variety of 3,4-disubstituted pyridine derivatives with a tertbutyl group in the 4-position were synthesized in a transition-metal-free, two-step reaction sequence from 3-substituted pyridine precursors. Highly regioselective addition of t-Bu2Mg to TIPS-activated pyridines and an efficient microwave-assisted aromatization with sulfur as oxidant afforded the desired 3,4-disubstituted pyridine derivatives in moderate to excellent yields. The method is compatible with many functional groups such as ester, amide, halide, nitrile or alkyne groups present in the 3-position.
引用
收藏
页码：4055 / 4064
页数：10
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