Construction of pyrazolo[3,4-b]pyridines and pyrazolo[4,3-c]pyridines by ring closure of 3-acylpyridine N-oxide tosylhydrazones

被引：24

作者：

Lominac, William J. ^{[1
]}

D'Angelo, Megan L. ^{[1
]}

Smith, Mark D. ^{[2
]}

Ollison, Darius A. ^{[1
]}

Hanna, James M., Jr. ^{[1
]}

机构：

[1] Winthrop Univ, Dept Chem Phys & Geol, Rock Hill, SC 29733 USA

[2] Univ S Carolina, Dept Chem & Biochem, Columbia, SC 29208 USA

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 08期

关键词：

Pyrazolo[3,4-b]pyridines; Pyrazolo[4,3-c]pyridines; Pyridine N-oxide hydrazones; Cyclization; SYNTHASE KINASE-3 GSK-3; ONE-STEP CONVERSION; BIOLOGICAL EVALUATION; SELECTIVE INHIBITORS; POTENT INHIBITORS; DERIVATIVES; PYRIDINES; FLUORINATION; ANTAGONISTS; QUINOLINES;

D O I：

10.1016/j.tetlet.2011.12.055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Acylpyridine N-oxide tosylhydrazones give good overall yields of a mixture of pyrazolo[3,4-b]pyridines and pyrazolo[4,3-c]pyridines when treated with an electrophilic additive and an amine base. (Z)-Hydrazones cyclize readily, while (E)-hydrazones fail to react under the reported conditions. The reaction takes place at room temperature, and moderate regiocontrol over the cyclization can be achieved by varying the electrophile/solvent combination. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：906 / 909

页数：4

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