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Chemistry of Heterocyclic Compounds

, Volume 19, Issue 11, pp 1163–1166 | Cite as

5,6-Condensed 3-nitropyridines from heterocyclic amines and nitromalonaldehyde

  • H. Schäfer
  • K. Gewald
  • M. Schmidt
Article

Abstract

The reaction of nitromalonaldehyde with 2-aminothiophenes leads to 5-nitrothieno-[2,3-b]pyridines. The analogous reaction with 3-aminopyrroles leads to 6-nitropyrrolo [3,2-b]pyridines. The analogous reaction with 4- and 5-aminopyrazoles leads to 6-nitropyrazolo[4,3-b]pyridines and 5-nitropyrazolo[3,4-b]pyridines, respectively. Enamines are formed as intermediates. 3- and 5-Aminopyrazoles which are unsubstituted at N-1 are converted to 3-nitropyrazolo[1,5-a]pyrimidines. The nitro derivatives obtained may be reduced to the corresponding amines.

Keywords

Organic Chemistry Pyridine Pyrimidine Enamine Analogous Reaction 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • H. Schäfer
    • 1
  • K. Gewald
    • 1
  • M. Schmidt
    • 1
  1. 1.Technical UniversityDresdenGerman Democratic Republic

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