Cycloaddition of N-Sulfonylpyridinium Imides and Isoquinolinium Imides with Acetylenedicarboxylates: A Practical Synthesis of Pyrazolo[1,5-a]pyridine and Pyrazolo[5,1-a]isoquinoline Derivatives

Chunrui Wu; Qingbo Wang; Jingjing Zhao; Pan Li; Feng Shi

doi:10.1055/s-0032-1316767

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(19): 3033-3042
DOI: 10.1055/s-0032-1316767

paper

Cycloaddition of N-Sulfonylpyridinium Imides and Isoquinolinium Imides with Acetylenedicarboxylates: A Practical Synthesis of Pyrazolo[1,5-a]pyridine and Pyrazolo[5,1-a]isoquinoline Derivatives

Chunrui Wu

Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan 475004, P. R. of China , Fax: +86(378)2864665 eMail: fshi@henu.edu.cn

,

Qingbo Wang

Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan 475004, P. R. of China , Fax: +86(378)2864665 eMail: fshi@henu.edu.cn

,

Jingjing Zhao

Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan 475004, P. R. of China , Fax: +86(378)2864665 eMail: fshi@henu.edu.cn

,

Pan Li

Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan 475004, P. R. of China , Fax: +86(378)2864665 eMail: fshi@henu.edu.cn

,

Feng Shi*

Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan 475004, P. R. of China , Fax: +86(378)2864665 eMail: fshi@henu.edu.cn

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Abstract

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Abstract

With the introduction of a sulfonyl group on the exocyclic nitrogen, pyridinium imides can undergo smooth [3+2] cycloaddition with electron-deficient alkynes to afford pyrazolo[1,5-a]pyridine derivatives after elimination of the sulfonyl group. The transformation operates with easy-to-handle substrates under mild conditions and brings the yields to a synthetically practical level. In situ generated isoquinolinium imides can also produce pyrazolo[5,1-a]isoquinolines in a similar fashion.

Key words

dipolar cycloaddition - heterocycles - azomethine imine - pyrazolo[1,5-a]pyridine - tandem reaction

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Referenzen

References

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