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The Biginelli reaction is a one-pot (three-component) procedure that in the presence of an acid catalyst, converts a β-keto ester, an aryl aldehyde, and urea to a hexahydropyrimidine derivative. First, urea reacts with the aldehyde affording an aminal, which dehydrates to an N-acyliminium ion. The enol form of the β-keto ester then attacks the N-acyliminium intermediate, making an open chain ureide, which cyclizes to a hexahydropyrimidine derivative.
- Reagents: Catalytic Acid (HCl, H2SO4, TsOH, LiBr, etc.), Alcohol Solvent (e.g. Ethanol)
- Reactant: β-Keto Ester, Aryl/Heteroaromatic/Aliphatic Aldehyde, Urea (Monosubstituted, Thiourea)
- Product: Hexahydropyrimidine Derivative
- Type of Reaction: Condensation
- Highly Enantioselective Organocatalytic Biginelli Reaction. Am. Chem. Soc. 2006, 128 (46), 14802–14803.
- Lanthanide Triflate Catalyzed Biginelli Reaction. One-Pot Synthesis of Dihydropyrimidinones under Solvent-Free Conditions. J. Org. Chem. 2000, 65 (12), 3864-3868.
- Biginelli Pyrimidone synthesis
- Passerini Reaction
- Ugi Reaction
- Multicomponent Reactions