Selective synthesis of pyrazolo[5,1-a]isoquinolines via 1,3-dipolar cycloaddition reaction

doi:10.1016/j.tetlet.2016.04.037

Tetrahedron Letters

Volume 57, Issue 21, 25 May 2016, Pages 2257-2261

https://doi.org/10.1016/j.tetlet.2016.04.037 Get rights and content

Highlights

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Two H-pyrazolo[5,1-a]isoquinolines are synthesized from the same 1,3-dipolars.
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Two heterocyclic frameworks are constructed simultaneously.
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Mild reaction conditions, readily available substrates.

Abstract

A novel and efficient route for the generation of pyrazolo[5,1-a]isoquinolines via 1,3-dipolar cycloaddition reaction of 1,3-dipolar and ethyl acetoacetate is described. Meanwhile, the selective synthesis of either pyrazolo[5,1-a]isoquinoline-1-carboxylate or 2-(pyrazolo[5,1-a]isoquinolin-2-yl)acetate derivatives from the same reactants has been achieved by simply varying base and reaction conditions.

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Section snippets

Acknowledgments

The generous financial support from the National Natural Science Foundation of China (Nos. 21372070 and 21471052), the Hunan Provincial Education Department Scientific Research Fund (No. 14k035) are gratefully acknowledged. We thank Dr Xiaodi Yang for her help in X-ray structural analysis.

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Selective synthesis of pyrazolo[5,1-a]isoquinolines via 1,3-dipolar cycloaddition reaction

Highlights

Abstract

Graphical abstract

Section snippets

Acknowledgments

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