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

页码：4055 / 4064

页数：10

共 48 条

[1] Microwave-assisted oxidative aromatization of Hantzsch 1,4-dihydropyridines using manganese dioxide [J].