Regioselective Metalation and Functionalization of the Pyrazolo[1,5-a]pyridine Scaffold Using Mg- and Zn-TMP Bases

被引：28

作者：

Balkenhohl, Moritz ^{[1
]}

Salgues, Bruno ^{[1
]}

Hirai, Takahiro ^{[1
]}

Karaghiosoff, Konstantin ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

[1] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13,Haus F, D-81377 Munich, Germany

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 10期

关键词：

DIRECTED-ORTHO-METALATION; FRUSTRATED LEWIS PAIRS; HETEROCYCLIC CHEMISTRY; FULL FUNCTIONALIZATION; AZAINDOLE DERIVATIVES; RECEPTOR ANTAGONISTS; SELECTIVE METALATION; N-HETEROCYCLES; MAGNESIUM; DISCOVERY;

D O I：

10.1021/acs.orglett.8b01204

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regioselective functionalization of the pyrazolo[1,5-a]pyridine scaffold using Mg- and Zn-TMP bases (TMP = 2,2,6,6-tetramethylpiperidyl) in the presence or absence of BF3 center dot OEt2 is described. Also, various functionalized pyrazolo[1,5-a]pyridines bearing an ester function (and an NHBoc or ethyl group) are magnesiated and functionalized, leading to polysubstituted heterocycles. Additionally, a sulfoxide directed ortho-metalation, followed by the transition-metal-free amination of a pyrazolo[1,5-a]pyridine sulfoxide, using a magnesium amide, is reported.

引用

页码：3114 / 3118

页数：5

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