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Synthesis 2015; 47(20): 3139-3146
DOI: 10.1055/s-0034-1381010
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Synthesis of 1H-Pyrazolo[4,3-c]quinolines and 4-Anilinoquinoline-3-carbonitriles from 4-Chloroquinoline-3-carbaldehydes

Chao Wang
Department of Chemistry, Fudan University, 200433 Shanghai, P. R. of China   Email: qrwang@fudan.edu.cn
,
Caifei Tang
Department of Chemistry, Fudan University, 200433 Shanghai, P. R. of China   Email: qrwang@fudan.edu.cn
,
Zhiming Li
Department of Chemistry, Fudan University, 200433 Shanghai, P. R. of China   Email: qrwang@fudan.edu.cn
,
Quanrui Wang*
Department of Chemistry, Fudan University, 200433 Shanghai, P. R. of China   Email: qrwang@fudan.edu.cn
› Author Affiliations
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Publication History

Received: 13 March 2015

Accepted after revision: 17 May 2015

Publication Date:
16 July 2015 (online)

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Abstract

Novel 1H-pyrazolo[4,3-c]quinolines and 4-anilinoquinoline-3-carbonitriles were prepared from readily accessible 4-chloroquinoline-3-carbaldehyde hydrazones by palladium-catalyzed intramolecular C–N bond formation and concurrent hydrazine N–N bond fission. These two classes of functionalized quinolines were chromatographically separable, and both are of biological interest. The ratio of the two products was found to be temperature-dependent; by changing the reaction temperature, either the pyrazoloquinoline or the anilinoquinolinecarbonitrile can become the dominant product.

Key words

hydrazones - palladium - cross-coupling - fused-ring systems - nitriles - pyrazoloquinolines

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1381010.
  • Supporting Information
 

  • References and Notes

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