Synthesis of Pyrazole involves methods like Knorr synthesis using 1,3-dicarbonyl compounds and hydrazines.
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Condensation of 1,3-Dicarbonyl Compounds with Hydrazine (most common method)
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Reactants:
- 1,3-diketones (e.g., acetylacetone)
- Hydrazine (NH₂NH₂) or substituted hydrazines
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Reaction:
- CH₃COCH₂COCH₃ + NH₂NH₂ → 3,5-Dimethylpyrazole + H₂O
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Mechanism:
- Formation of hydrazone at one carbonyl
- Intramolecular cyclization
- Elimination of water → Pyrazole ring
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Advantages:
- Simple, high-yielding, allows substitution at 3 and 5 positions
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Knorr Pyrazole Synthesis
- Reactants: α-hydrazino ketones + β-ketoesters
- Use: For substituted pyrazoles with varying groups at C-3 and C-5
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From α,β-unsaturated ketones and hydrazines
- Hydrazine adds to the double bond and then cyclizes.
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