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Synthesis of pyrazolo[3,4-c]isoquinoline and pyrazolo[3,4-b]pyridine derivatives from azomethines and CH-acidic compounds

Synthese von Pyrazolo[3,4-c]isochinolin- und Pyrazolo[3,4-b]pyridin-Derivaten aus Azomethinen und CH-aciden Verbindungen

  • Organische Chemie Und Biochemie
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Summary

Donor substituted arylidene aminopyrazoles1a–c and CH-acidic 1,3-dicarbonyl compounds2a–e give in ethanol in an addition/cyclization reaction pyrazolo[3,4-c]isoquinolines4a–i and pyrazolo[3,4-b]pyridine derivatives5a,b, respectively. Using ethyl cyanoacetate as CH-acidic component, cinnamate6 and the cyano substituted pyrazolo[3,4-b]pyridine7 are formed.

Zusammenfassung

Die Reaktion der donorsubstituierten Aryliden-aminopyrazole1a–c mit den CH-aciden 1,3-Dicarbonylverbindungen2a–e führt in einer Additions/Cyclisierungsreaktion zu den Pyrazolo[3,4-c]isochinolin-4a–i bzw. Pyrazolo[3,4-b]pyridin-Derivaten5a,b. Verwendet man Cyanessigester als CH-acide Komponente, werden der Zimtsäureester6 und das cyanosubstituierte Pyrazolo[3,4-b]pyridin7 gebildet.

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References

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Authors and Affiliations

  1. Fachbereich Chemie, Universität Leipzig, D-04103, Leipzig, Germany

    Lothar Hennig, Mario Alva-Astudillo, Reinhard Meusinger & Gerhard Mann

Authors
  1. Lothar Hennig
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  2. Mario Alva-Astudillo
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  3. Reinhard Meusinger
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  4. Gerhard Mann
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Hennig, L., Alva-Astudillo, M., Meusinger, R. et al. Synthesis of pyrazolo[3,4-c]isoquinoline and pyrazolo[3,4-b]pyridine derivatives from azomethines and CH-acidic compounds. Monatsh Chem 124, 893–898 (1993). https://doi.org/10.1007/BF00816412

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  • DOI: https://doi.org/10.1007/BF00816412

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