Synthesis of Pyrazole

Synthesis of Pyrazole involves methods like Knorr synthesis using 1,3-dicarbonyl compounds and hydrazines.

  1. Condensation of 1,3-Dicarbonyl Compounds with Hydrazine (most common method)

    • Reactants:

      • 1,3-diketones (e.g., acetylacetone)
      • Hydrazine (NH₂NH₂) or substituted hydrazines
    • Reaction:

      • CH₃COCH₂COCH₃  +  NH₂NH₂  →  3,5-Dimethylpyrazole  +  H₂O
    • Synthesis of Pyrazole
    • Mechanism:

      • Formation of hydrazone at one carbonyl
      • Intramolecular cyclization
      • Elimination of water → Pyrazole ring
    • Advantages:

      • Simple, high-yielding, allows substitution at 3 and 5 positions
  2. Knorr Pyrazole Synthesis

    • Reactants: α-hydrazino ketones + β-ketoesters
    • Use: For substituted pyrazoles with varying groups at C-3 and C-5
  3. From α,β-unsaturated ketones and hydrazines

    • Hydrazine adds to the double bond and then cyclizes.

Thank you for reading from Firsthope's notes, don't forget to check YouTube videos!

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.